1-tridecyl-2,3-epoxypropan-1-ol | 203924-96-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-tridecyl-2,3-epoxypropan-1-ol
• 英文别名: 1-(Oxiran-2-yl)tetradecan-1-ol
• CAS: 203924-96-3
• 化学式: C₁₆H₃₂O₂
• 分子量: 256.429
• InChiKey: QJEODLKTFPNHFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  18
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-tridecyl-2,3-epoxypropan-1-ol 在 二氯二茂钛 、 4-甲基苯磺酸吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 6.0h， 生成 2-tridecyl-3-((tetrahydropyranyloxy)methyl)-4-methylenetetrahydrofuran
  参考文献：
  名称：

  Stereoselective Synthesis of Polysubstituted Tetrahydrofurans by Radical Cyclization of Epoxides Using a Transition-Metal Radical Source. Application to the Total Synthesis of (±)-Methylenolactocin and (±)-Protolichesterinic Acid

  摘要：

  Radical cyclization reactions of substituted alpha-(prop-2-ynyloxy) epoxides using bis(cyclopentadienyl)-titanium(III) chloride as the radical source resulted in polysubstituted tetrahydrofurans. Titanium(III) species were prepared in situ from commercially available titanocene dichloride and zinc dust in tetrahydrofuran, Upon radical cyclization, 2-aryl epoxides 3a-e afforded only trans products 4a-e whereas the 2-alkyl epoxides 3f-h formed a mixture of isomeric products 4f-h in a ratio of 5:1. Some of the aryl tetrahydrofuran derivatives have already been used for the synthesis of bioactive furofuran lignans. 2-Pentyl-3-(hydroxymethyl)-4-methylenetetrahydrofuran (4f) and 2-tridecyl-3-(hydroxymethyl)-4-methylenetetrahydrofuran (4g) have been transformed to two antitumor antibiotics (+/-)-methylenolactocin (1f) and (+/-)-protolichesterinic acid (1g), respectively, in good overall yield.

  DOI：

  10.1021/jo971526d
• 作为产物：
  描述：

  rac-hexadecen-3-ol 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 以85%的产率得到1-tridecyl-2,3-epoxypropan-1-ol
  参考文献：
  名称：

  Stereoselective Synthesis of Polysubstituted Tetrahydrofurans by Radical Cyclization of Epoxides Using a Transition-Metal Radical Source. Application to the Total Synthesis of (±)-Methylenolactocin and (±)-Protolichesterinic Acid

  摘要：

  Radical cyclization reactions of substituted alpha-(prop-2-ynyloxy) epoxides using bis(cyclopentadienyl)-titanium(III) chloride as the radical source resulted in polysubstituted tetrahydrofurans. Titanium(III) species were prepared in situ from commercially available titanocene dichloride and zinc dust in tetrahydrofuran, Upon radical cyclization, 2-aryl epoxides 3a-e afforded only trans products 4a-e whereas the 2-alkyl epoxides 3f-h formed a mixture of isomeric products 4f-h in a ratio of 5:1. Some of the aryl tetrahydrofuran derivatives have already been used for the synthesis of bioactive furofuran lignans. 2-Pentyl-3-(hydroxymethyl)-4-methylenetetrahydrofuran (4f) and 2-tridecyl-3-(hydroxymethyl)-4-methylenetetrahydrofuran (4g) have been transformed to two antitumor antibiotics (+/-)-methylenolactocin (1f) and (+/-)-protolichesterinic acid (1g), respectively, in good overall yield.

  DOI：

  10.1021/jo971526d

文献信息

• Total synthesis of (±)-Dihydroprotolichesterinic acid and Formal synthesis of (±)-Roccellaric acid by radical cyclisation of an epoxide. Using a transition-metal radical source
  作者：Pijus Kumar Mandal、Subhas Chandra Roy

  DOI：10.1016/s0040-4020(99)00635-3

  日期：1999.9

  A short and efficient total synthesis of (±)-Dihydroprotolichesterinic acid (1) and Formal synthesis of (±)-Roccellaric acid (2) has been acheived by radical cyclisation of epoxide using a transition metal radical source.

  通过使用过渡金属自由基源对环氧化物进行自由基环化，已实现了一种短而有效的全合成（±）-二氢脯脂酸原酸（1）和（±）-二十碳烯酸（2）的形式合成。
• THERMOPLASTIC RESIN FILM WITH SATISFACTORY PRINTABILITY
  申请人：Yupo Corporation

  公开号：EP1172400A1

  公开（公告）日：2002-01-16

  Described is a thermoplastic resin film having on a surface thereof a hydroxy-modified imine polymer containing repeating units represented by the following general formula (I) in an amount of 5 mol% or more based on the total of repeating units. This thermoplastic resin film has ink transfer, adhesion and aging stability, and excellent printability of generating no back ghost when offset printing using oxidation polymerization type ink is performed on both faces.

  所述的是一种热塑性树脂薄膜，其表面含有羟基改性亚胺聚合物，该聚合物含有以下通式 (I) 所代表的重复单元，其含量为重复单元总量的 5 mol% 或以上。这种热塑性树脂薄膜具有油墨转移性、附着性和老化稳定性，而且在使用氧化聚合型油墨进行胶版印刷时，两面都不会产生重影，具有极佳的印刷适性。
• Thermoplastic resin film satisfactory in printability
  申请人：YUPO CORPORATION

  公开号：US20020054991A1

  公开（公告）日：2002-05-09

  Described is a thermoplastic resin film having on a surface thereof a hydroxy-modified imine polymer containing repeating units represented by the following general formula (I) in an amount of 5 mol % or more based on the total of repeating units. This thermoplastic resin film has ink transfer, adhesion and aging stability, and excellent printability of generating no back ghost when offset printing using oxidation polymerization type ink is performed on both faces 1 .

  所述热塑性树脂薄膜的表面含有羟基改性亚胺聚合物，该聚合物含有以下通式 (I) 所代表的重复单元，其含量为重复单元总量的 5 mol % 或以上。这种热塑性树脂薄膜具有油墨转移性、附着性和老化稳定性，并且在使用氧化聚合型油墨进行胶版印刷时，两面都不会产生重影，具有优异的印刷适性。 1 .
• US6586106B2
  申请人：——

  公开号：US6586106B2

  公开（公告）日：2003-07-01
• [EN] INORGANIC OXIDE PARTICLE DISPERSION, MOLDING COMPOSITION IN WHICH SAME IS USED, AND MOLDED ARTICLE<br/>[FR] DISPERSION DE PARTICULES D'OXYDE INORGANIQUE, COMPOSITION DE MOULAGE DANS LAQUELLE ELLE EST UTILISÉE, ET ARTICLE MOULÉ<br/>[JA] 無機酸化物粒子分散体およびそれを用いた成型用組成物、成型体
  申请人：TOYO INK SC HOLDINGS CO LTD

  公开号：WO2021039529A1

  公开（公告）日：2021-03-04

  無機酸化物粒子と、分散剤と、アルコキシシラン化合物と、沸点２００℃以上の重合性不飽和基を有しない可塑剤とを含有する無機酸化物粒子分散体であって、前記分散剤が、下記一般式Ａで表される分散剤Ａ、および下記一般式Ｂで表される分散剤Ｂからなる群より選ばれる少なくとも１種を含む無機酸化物粒子分散体。