1,1-Bis-(ethoxycarbonyl)-3-ethyl-cyclobutan | 66016-02-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,1-Bis-(ethoxycarbonyl)-3-ethyl-cyclobutan
• 英文别名: 1,1-bis(ethoxycarbonyl)-3-ethyl cyclobutane；3-ethyl-1,1-dicarbethoxycyclobutane；Diethyl 3-ethylcyclobutane-1,1-dicarboxylate
• CAS: 66016-02-2
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: NHDOSBGQQMXBQB-UHFFFAOYSA-N

物化性质

• 沸点：
  257.0±13.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2917209090

反应信息

• 作为反应物：
  描述：

  1,1-Bis-(ethoxycarbonyl)-3-ethyl-cyclobutan 在 氢氧化钾 、 thallium (I) ethoxide 作用下， 反应 2.0h， 生成 norethisterone 3-ethylcyclobutylcarboxylate
  参考文献：
  名称：

  Long-acting contraceptive agents: Cyclopropyl and cyclobutyl esters of norethisterone

  摘要：

  Several esters of norethisterone (17 alpha-ethynyl-17 beta-hydroxyestr-4-en-3-one) with carboxylic acids containing a cyclopropyl or cyclobutyl ring have been synthesized and the stereochemistries of the side-chains determined.

  DOI：

  10.1016/0039-128x(83)90100-9
• 作为产物：
  描述：

  2-乙基-1,3-丙二醇 在 sodium 作用下， 以 吡啶 、 xylene 为溶剂， 反应 38.0h， 生成 1,1-Bis-(ethoxycarbonyl)-3-ethyl-cyclobutan
  参考文献：
  名称：

  Long-acting contraceptive agents: Cyclopropyl and cyclobutyl esters of norethisterone

  摘要：

  Several esters of norethisterone (17 alpha-ethynyl-17 beta-hydroxyestr-4-en-3-one) with carboxylic acids containing a cyclopropyl or cyclobutyl ring have been synthesized and the stereochemistries of the side-chains determined.

  DOI：

  10.1016/0039-128x(83)90100-9

文献信息

• Preparation of 15-deoxy-16-hydroxyprostaglandins
  申请人：Miles Laboratories, Inc.

  公开号：US04132738A1

  公开（公告）日：1979-01-02

  Analogues of PGE.sub.1 having the structural formula, ##STR1## in which J is R-hydroxymethylene or S-hydroxymethylene; R.sub.1 is hydrogen; R.sub.2 is hydrogen or together with R.sub.4 is a methylene chain of 2 to 3 carbon atoms such that a cycloalkyl of 5 to 6 carbon atoms inclusive is formed; R.sub.3 is hydrogen or methyl, or together with R.sub.4 is a methylene or a lower alkylated methylene chain of 2 to 5 carbon atoms such that a cycloalkyl or a lower alkylated cycloalkyl of 4 to 7 carbon atoms inclusive is formed, or together with R.sub.4 is bicycloalkyl or bicycloalkenyl moiety having the formula: ##STR2## SUCH THAT A BICYCLOALKYL OR BICYCLOALKENYL COMPOUND IS FORMED, WHEREIN M AND N ARE INTEGERS HAVING A VALUE FROM 0 TO 3, P IS AN INTEGER HAVING A VALUE FROM 0 TO 4 AND Q IS AN INTEGER HAVING A VALUE OF FROM 1 TO 4 AND WHEREIN THE DOUBLE BOND OF SUCH BICYCLOALKENYL IS IN THE M, N, P, OR Q BRIDGE; R.sub.4 is hydrogen or methyl or together with R.sub.2 or R.sub.3 forms a cycloalkyl or bicycloalkyl or bicycloalkenyl as defined above, or together with R.sub.5 is a methylene chain of 3 to 5 carbon atoms such that a cycloalkyl of 4 to 6 carbon atoms inclusive is formed; R.sub.5 is selected from the group consisting of hydrogen, straight-chain alkyl having from 1 to 3 carbon atoms or together with R.sub.4 forms a cycloalkyl as defined above; and R.sub.6 is hydrogen or straight-chain alkyl having from 1 to 3 carbon atoms are disclosed. Pge.sub.1 ester analogues of the above formula, limited to the structures wherein two of R.sub.2, R.sub.3 R.sub.4 and R.sub.5 form a cycloalkyl, lower alkylated cycloalkyl, bicycloalkyl or bicycloalkenyl are also disclosed. The prostaglandin analogues selectively produce bronchodilation and decrease gastric secretion in vivo. Methods of preparing the analogues and starting materials required in the synthesis of the analogues are also disclosed.

  具有结构式##STR1##的PGE.sub.1的类似物，其中J是R-羟甲亚甲基或S-羟甲亚甲基；R.sub.1是氢；R.sub.2是氢或与R.sub.4一起是2到3个碳原子的亚甲基链，形成包括5到6个碳原子的环烷基；R.sub.3是氢或甲基，或与R.sub.4一起是2到5个碳原子的亚甲基或低烷基化亚甲基链，形成包括4到7个碳原子的环烷基或低烷基化环烷基，或与R.sub.4一起是具有式子的双环烷基或双环烯基基团：##STR2##形成双环烷基或双环烯基化合物，其中M和N是具有值从0到3的整数，P是具有值从0到4的整数，Q是具有值从1到4的整数，且此类双环烯基的双键位于M、N、P或Q桥上；R.sub.4是氢或甲基，或与R.sub.2或R.sub.3一起形成如上定义的环烷基或双环烷基或双环烯基，或与R.sub.5一起是3到5个碳原子的亚甲基链，形成包括4到6个碳原子的环烷基；R.sub.5选自由氢、具有1到3个碳原子的直链烷基或与R.sub.4一起形成如上定义的环烷基；R.sub.6是氢或具有1到3个碳原子的直链烷基。上述结构的Pge.sub.1酯类似物，限于其中两个R.sub.2、R.sub.3、R.sub.4和R.sub.5形成环烷基、低烷基化环烷基、双环烷基或双环烯基的结构也被披露。这些前列腺素类似物在体内选择性地产生支气管扩张并减少胃分泌。还披露了制备这些类似物以及合成这些类似物所需的起始物料的方法。
• Cyclobutyl substituted derivatives of prostaglandin analogs
  申请人：Miles Laboratories, Inc.

  公开号：US04220795A1

  公开（公告）日：1980-09-02

  Novel C15 cyclobutyl analogs or derivatives of prostaglandins of the E-, A- and F-classes are useful modifiers of smooth muscle activity. The compounds have valuable pharmacological properties such as platelet antiaggregating agents, gastric antisecretory agents and brochodilating agents.

  新型C15环丁基类前列腺素的衍生物或类似物在调节平滑肌活动方面具有用途。这些化合物具有宝贵的药理特性，如抗血小板聚集剂、胃抗分泌剂和支气管扩张剂。
• Methyl 11alpha,15R-dihydroxy-16,18-methano-16-methyl-9-oxoprost-13E-en-1-oate, a process for its production and composition containing it
  申请人：MILES LABORATORIES, INC.

  公开号：EP0036436A1

  公开（公告）日：1981-09-30

  Disclosed is methyl 11a,15R-dihydroxy-16,18-metha- no-16-methyl-9-oxoprost-13E-en-1-oate of the formula: This compound is a potent bronchodilator and because it is less irritating to the tracheobronchical tract than PGE,, it is useful in the treatment of asthma.

  所公开的是式 11a,15R-二羟基-16,18-甲基-9-氧前列素-13E-烯-1-酸甲酯： 这种化合物是一种强效支气管扩张剂，由于它对气管支气管的刺激性比 PGE 小，因此可用于治疗哮喘。
• Potent ketoamide inhibitors of HCV NS3 protease derived from quaternized P1 groups
  作者：Srikanth Venkatraman、Francisco Velazquez、Wanli Wu、Melissa Blackman、Vincent Madison、F. George Njoroge

  DOI：10.1016/j.bmcl.2010.02.051

  日期：2010.4

  Blood borne hepatitis C infections are the primary cause for liver cirrhosis and hepatocellular carcinoma. HCV NS3 protease, a pivotal enzyme in the replication cycle of HCV virus has been the primary target for development of new drug candidates. Boceprevir and telaprevir are two novel ketoamide derived inhibitors that are currently undergoing phase-III clinical trials. These inhibitors include ketoamide functionality as serine trap and have an acidic alpha-ketoamide center that undergoes epimerization under physiological conditions. Our initial attempts to arrest this epimerization by introducing quaternary amino acids at P-1 had resulted in significantly diminished activity. In this manuscript we describe alpha quaternized P-1 group that result in potent inhibitors in the enzyme assay and demonstrate cellular activity comparable to boceprevir. (C) 2010 Elsevier Ltd. All rights reserved.
• Chain, L. K. M.; Gemmel, P. A.; Gray, G. W., Molecular Crystals and Liquid Crystals (1969-1991), 1987, vol. 147, p. 113 - 140
  作者：Chain, L. K. M.、Gemmel, P. A.、Gray, G. W.、Lacey, D.、Toyne, K. J.

  DOI：——

  日期：——