TRANS-CYCLOHEXANE-1,4-DICARBOXYLIC ACID DIAMIDE | 54657-09-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: TRANS-CYCLOHEXANE-1,4-DICARBOXYLIC ACID DIAMIDE
• 英文别名: trans-1,4-di(carboxamido)cyclohexane；trans-cyclohexane-dicarboxylic acid-(1.4)-diamide；trans-Cyclohexan-dicarbonsaeure-(1.4)-diamid；trans-1,4-Cyclohexandicarboxamid
• CAS: 54657-09-9
• 化学式: C₈H₁₄N₂O₂
• 分子量: 170.211
• InChiKey: ZWUNKULTLYLLTH-IZLXSQMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.24
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  86.18
• 氢给体数：
  2.0
• 氢受体数：
  2.0

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  TRANS-CYCLOHEXANE-1,4-DICARBOXYLIC ACID DIAMIDE 在 sodium hydroxide 、 溴 作用下， 生成 trans-1,4-Diaminocyclohexane
  参考文献：
  名称：

  Synthesis of analogs of N-(2-chloroethyl)-N'-(trans-4-methylcyclohexyl)-N-nitrosourea for evaluation as anticancer agents

  摘要：

  The superior activity of N-(2-chloroethyl)-N'-(trans-4-methylcyclohexyl)-N-nitrosourea (MeCCNU) against advanced murine Lewis lung carcinoma in comparisons with the cis form and other nitrosoureas prompted the synthesis of a number of MeCCNU analogues, including several cis-trans pairs. The methyl group was replaced by a variety of substituents (CO2H, CH2CO2H, CO2Me, CH2OAc, CH2Cl, OMe); the trans-3-methylcyclohexyl, cis-2-methyl-1,3-dithian-5-yl, cis- and trans-2-methyl-1,3-dithian-5-yl-tetraoxide, and 1-methylhexyl (open-chain) analogues were also prepared. Preliminary tests against murine leukemia L1210 revealed therapeutic indices (ED50/LD10) ranging from 0.26 to 0.79; all but three analogues effected 50% cure rates at nontoxic doses, the open-chain analogue being one of the least active. In terms of therapeutic index, diequatorial (trans-4) isomers were, with one exception, as active as or, in four of the eight examples, somewhat more active than the corresponding axial-equatorial (cis-4) isomers. In this series, four of the five 2-fluoroethyl analogues prepared were clearly inferior to the corresponding 2-chloroethyl analogues.

  DOI：

  10.1021/jm00212a019
• 作为产物：
  描述：

  CYCLOHEXANE-1,4-DICARBONITRILE 生成 TRANS-CYCLOHEXANE-1,4-DICARBOXYLIC ACID DIAMIDE
  参考文献：
  名称：

  Synthesis of analogs of N-(2-chloroethyl)-N'-(trans-4-methylcyclohexyl)-N-nitrosourea for evaluation as anticancer agents

  摘要：

  The superior activity of N-(2-chloroethyl)-N'-(trans-4-methylcyclohexyl)-N-nitrosourea (MeCCNU) against advanced murine Lewis lung carcinoma in comparisons with the cis form and other nitrosoureas prompted the synthesis of a number of MeCCNU analogues, including several cis-trans pairs. The methyl group was replaced by a variety of substituents (CO2H, CH2CO2H, CO2Me, CH2OAc, CH2Cl, OMe); the trans-3-methylcyclohexyl, cis-2-methyl-1,3-dithian-5-yl, cis- and trans-2-methyl-1,3-dithian-5-yl-tetraoxide, and 1-methylhexyl (open-chain) analogues were also prepared. Preliminary tests against murine leukemia L1210 revealed therapeutic indices (ED50/LD10) ranging from 0.26 to 0.79; all but three analogues effected 50% cure rates at nontoxic doses, the open-chain analogue being one of the least active. In terms of therapeutic index, diequatorial (trans-4) isomers were, with one exception, as active as or, in four of the eight examples, somewhat more active than the corresponding axial-equatorial (cis-4) isomers. In this series, four of the five 2-fluoroethyl analogues prepared were clearly inferior to the corresponding 2-chloroethyl analogues.

  DOI：

  10.1021/jm00212a019

文献信息

• METHOD FOR PRODUCING TRANS-BIS(AMINOMETHYL)CYCLOHEXANE, METHOD FOR PRODUCING BIS(ISOCYANATOMETHYL)CYCLOHEXANE, BIS(ISOCYANATOMETHYL)CYCLOHEXANE, POLYISOCYANATE COMPOSITION, AND POLYURETHANE RESIN
  申请人：MITSUI CHEMICALS, INC.

  公开号：US20160207875A1

  公开（公告）日：2016-07-21

  A method for producing trans-bis(aminomethyl)cyclohexane includes a trans-isomerization step in which cis-dicyanocyclohexane is isomerized into trans-dicyanocyclohexane by heating dicyanocyclohexane containing cis-dicyanocyclohexane in the presence of a tar component produced by distillation of dicyanocyclohexane; and an aminomethylation step in which trans-dicyanocyclohexane produced by the trans-isomerization step is allowed to contact with hydrogen to produce trans-bis(aminomethyl)cyclohexane.

  生产反式-双(氨甲基)环己烷的方法包括以下步骤：在一个反式异构化步骤中，通过加热含有顺-二氰基环己烷的二氰基环己烷，在二氰基环己烷的蒸馏产生的焦油组分的存在下，将顺-二氰基环己烷异构化为反-二氰基环己烷；以及在一个氨甲基化步骤中，通过让通过反式异构化步骤产生的反-二氰基环己烷与氢接触来产生反式-双(氨甲基)环己烷。
• METHOD FOR PRODUCING TRANS-1,4-BIS(AMINOMETHYL) CYCLOHEXANE
  申请人：Yoshimura Naritoshi

  公开号：US20130197270A1

  公开（公告）日：2013-08-01

  A method for producing trans-1,4-bis(aminomethyl)cyclohexane includes a nuclear hydrogenation step of producing a hydrogenated terephthalic acid or terephthalic acid derivative by nuclear hydrogenation of a terephthalic acid or terephthalic acid derivative, the terephthalic acid or terephthalic acid derivative being at least one selected from the group consisting of terephthalic acid, terephthalic acid ester, and terephthalic acid amide; a cyanation step of treating the hydrogenated terephthalic acid or terephthalic acid derivative with ammonia, thereby producing 1,4-dicyanocyclohexane, and producing trans-1,4-dicyanocyclohexane from the obtained 1,4-dicyanocyclohexane; and an aminomethylation step of treating the trans-1,4-dicyanocyclohexane with hydrogen, thereby producing trans-1,4-bis(aminomethyl)cyclohexane. Metal oxide is used as a catalyst in the cyanation step, and the obtained trans-1,4-dicyanocyclohexane has a metal content of 3000 ppm or less.

  生产trans-1,4-双(氨甲基)环己烷的方法包括以下步骤：通过对苯二甲酸或苯二甲酸衍生物进行核氢化反应，生产氢化苯二甲酸或苯二甲酸衍生物，所述苯二甲酸或苯二甲酸衍生物至少选自苯二甲酸、苯二甲酸酯和苯二甲酸酰胺组成的群体；通过将氢化的苯二甲酸或苯二甲酸衍生物与氨处理，从而生产1,4-二氰基环己烷，并从获得的1,4-二氰基环己烷生产trans-1,4-二氰基环己烷；通过将trans-1,4-二氰基环己烷与氢处理，从而生产trans-1,4-双(氨甲基)环己烷。在氰化步骤中使用金属氧化物作为催化剂，获得的trans-1,4-二氰基环己烷金属含量不超过3000 ppm。
• METHOD FOR PRODUCING BIS(AMINOMETHYL)CYCLOHEXANES
  申请人：Yoshimura Naritoshi

  公开号：US20130197269A1

  公开（公告）日：2013-08-01

  A method for producing bis(aminomethyl)cyclohexanes includes a nuclear hydrogenation step of producing hydrogenated phthalic acids or phthalic acid derivatives by nuclear hydrogenation of phthalic acids or phthalic acid derivatives of at least one selected from the group consisting of phthalic acids, phthalic acid esters, and phthalic acid amides; a cyanation step of treating the hydrogenated phthalic acids or phthalic acid derivatives obtained in the nuclear hydrogenation step with ammonia, thereby producing dicyanocyclohexanes; and an aminomethylation step of treating the dicyanocyclohexanes obtained in the cyanation step with hydrogen, thereby producing bis(aminomethyl)cyclohexanes. In the cyanation step, metal oxide is used as a catalyst, and the obtained dicyanocyclohexanes have a metal content of 3000 ppm or less.

  一种生产双(氨甲基)环己烷的方法，包括以下步骤：核氢化步骤，通过对邻苯二甲酸或邻苯二甲酸衍生物进行核氢化，得到氢化的邻苯二甲酸或邻苯二甲酸衍生物，所述邻苯二甲酸或邻苯二甲酸衍生物至少选自邻苯二甲酸、邻苯二甲酸酯和邻苯二甲酸酰胺组成的群体；青化步骤，将在核氢化步骤中获得的氢化邻苯二甲酸或邻苯二甲酸衍生物与氨处理，从而产生二氰基环己烷；氨甲基化步骤，将在青化步骤中获得的二氰基环己烷与氢处理，从而产生双(氨甲基)环己烷。在青化步骤中，使用金属氧化物作为催化剂，所获得的二氰基环己烷的金属含量为3000 ppm或更低。
• METHOD FOR PRODUCING DICYANOCYCLOHEXANE AND BIS(AMINOMETHYL)CYCLOHEXANE
  申请人：MITSUBISHI GAS CHEMICAL COMPANY, INC.

  公开号：US20200392072A1

  公开（公告）日：2020-12-17

  The problem addressed by this invention is to achieve a useful and novel method for producing dicyanocyclohexane and bis(aminomethyl)cyclohexane. This problem was solved by providing a method for producing dicyanocyclohexane having a cyanation step in which dicyanocyclohexane is obtained by a cyanation reaction of cyanocyclohexane-1-carboxylic acid and/or a salt thereof with an ammonia source, and a method for producing bis(aminomethyl)cyclohexane using the dicyanocyclohexane thus produced.

  本发明解决的问题是提供一种用于生产二氰基环己烷和双(氨甲基)环己烷的有用且新颖的方法。通过提供一种生产二氰基环己烷的方法，其中包括通过将氰基环己烷-1-羧酸及/或其盐与氨源进行氰化反应以获得二氰基环己烷的氰化步骤，并利用所生产的二氰基环己烷生产双(氨甲基)环己烷的方法，解决了该问题。
• 1,4-BIS(ISOCYANATOMETHYL)CYCLOHEXANE, POLYISOCYANATE COMPOSITION, POLYURETHANE RESIN, MOLDED PRODUCT, EYEWEAR MATERIAL, EYEWEAR FRAME AND LENS
  申请人：Mitsui Chemicals, Inc.

  公开号：EP3037411A1

  公开（公告）日：2016-06-29

  1,4-bis(isocyanatomethyl)cyclohexane contains 70 mol% or more and 95 mol% or less of a trans isomer relative to a total amount of a cis isomer and the trans isomer, and 0.1 ppm or more and 300 ppm or less of the compound represented by formula (1) below:

  相对于顺式异构体和反式异构体的总量，1,4-双（异氰酸基甲基）环己烷含有 70 摩尔%或以上和 95 摩尔%或以下的反式异构体，以及 0.1 ppm 或以上和 300 ppm 或以下的下式（1）所代表的化合物：

表征谱图