4-chloro-3,3-dimethoxy-butylic acid ethyl ester | 6567-42-6

• 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: 4-chloro-3,3-dimethoxy-butylic acid ethyl ester
• 英文别名: 4-chloro-3,3-dimethoxy-butyric acid ethyl ester；Aethyl-γ-chlor-β,β-dimethoxybutyrat；Ethyl 4-chloro-3,3-dimethoxybutanoate；ethyl 4-chloro-3,3-dimethoxybutanoate
• CAS: 6567-42-6
• 化学式: C₈H₁₅ClO₄
• 分子量: 210.658
• InChiKey: RTLKEYYMSIJFPA-UHFFFAOYSA-N

物化性质

• 沸点：
  101-103 °C(Press: 11 Torr)
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-chloro-3,3-dimethoxy-butylic acid ethyl ester 在 [RuCl2(benzene)]2 、 氢气 、 N,N'-羰基二咪唑 、 calcium carbonate 、 potassium hydroxide 、 (2,2,2',2'-tetramethyl[4,4'-bibenzo[d][1,3]dioxole]-5,5'-diyl)bis(diphenylphosphine) 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 55.0 ℃ 、6.0 MPa 条件下， 反应 23.0h， 生成 methyl 6-chloro-3-hydroxy-5,5-dimethoxyhexanoate
  参考文献：
  名称：

  Acid-labile δ-ketal-β-hydroxy esters by asymmetric hydrogenation of corresponding δ-ketal-β-keto esters in the presence of CaCO3

  摘要：

  通过Ru-SunPhos催化不对称氢化相应的ε-取代δ-酮缩酮-β-酮酯，获得了一系列酸不稳定的、光学纯的ε-取代δ-酮缩酮-β-羟基酯。在氢化反应中，CaCO3发挥了双重作用——清除催化剂形成过程中产生的酸，并保持催化剂的活性。

  DOI：

  10.1039/c2cc31002c
• 作为产物：
  描述：

  4-氯乙酰乙酸乙酯 、 原甲酸三甲酯 在 对甲苯磺酸 作用下， 反应 72.0h， 生成 4-chloro-3,3-dimethoxy-butylic acid ethyl ester
  参考文献：
  名称：

  A Novel Substitution Reaction of Tetrahydropyrano[3,4-b]indole Derivative — Chain Extension and Structural Correlation Study

  摘要：

  An unusual cyanation with rearrangement of a 1-chloromethyltetrahydropyrano[3,4-b]indole-1-acetic acid ester derivative is reported. The resulting C-1 chain extension product is identified by correlation studies and spectral method.

  DOI：

  10.3987/com-02-9703

文献信息

• Base-mediated hydrolytic cleavage with chain migration of 1-chloromethyl-tetrahydropyrano[3,4-b]indoles: an unusual pathway to 2-succinoyl tryptophols
  作者：Shan-Yen Chou、Ching-Hui Chen

  DOI：10.1016/j.tetlet.2006.06.105

  日期：2006.8

  An unusual hydrolytic cleavage with 1,2-alkyl chain migration of 1-chloromethyl-tetrahydropyrano[3,4-b]indoles by heating with a limited amount of water and base in DMF is reported. A mechanism for the formation of 1,2-alkyl chain migration products, 2-succinoyl tryptophols, and the ring-expansion products, dihydro-oxepine fused indoles, is reported. No comparable 1,2-chain migration from a structurally related 1-chloromethyl-isochroman is observed. (c) 2006 Elsevier Ltd. All rights reserved.
• Acid-labile δ-ketal-β-hydroxy esters by asymmetric hydrogenation of corresponding δ-ketal-β-keto esters in the presence of CaCO3
  作者：Weizheng Fan、Wanfang Li、Xin Ma、Xiaoming Tao、Xiaoming Li、Ying Yao、Xiaomin Xie、Zhaoguo Zhang

  DOI：10.1039/c2cc31002c

  日期：——

  A series of acid-labile, optically pure ε-substituted δ-ketal-β-hydroxy esters were obtained by a Ru-SunPhos catalyzed asymmetric hydrogenation of the corresponding ε-substituted δ-ketal-β-keto esters. CaCO3 played a dual role in the hydrogenation reaction—removing the acid generated during the formation of the catalyst and maintaining the activity of the catalyst.

  通过Ru-SunPhos催化不对称氢化相应的ε-取代δ-酮缩酮-β-酮酯，获得了一系列酸不稳定的、光学纯的ε-取代δ-酮缩酮-β-羟基酯。在氢化反应中，CaCO3发挥了双重作用——清除催化剂形成过程中产生的酸，并保持催化剂的活性。
• A Novel Substitution Reaction of Tetrahydropyrano[3,4-b]indole Derivative — Chain Extension and Structural Correlation Study
  作者：Shan-Yen Chou

  DOI：10.3987/com-02-9703

  日期：——

  An unusual cyanation with rearrangement of a 1-chloromethyltetrahydropyrano[3,4-b]indole-1-acetic acid ester derivative is reported. The resulting C-1 chain extension product is identified by correlation studies and spectral method.