1'-isopropyl-4'-chloro-2'(E)-butenyl 2-butenoate | 148680-94-8

• 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'-isopropyl-4'-chloro-2'(E)-butenyl 2-butenoate
• 英文别名: [(E)-6-chloro-2-methylhex-4-en-3-yl] but-2-ynoate
• CAS: 148680-94-8
• 化学式: C₁₁H₁₅ClO₂
• 分子量: 214.692
• InChiKey: MMJCSUNYNRJMGT-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1'-isopropyl-4'-chloro-2'(E)-butenyl 2-butenoate 在 palladium diacetate lithium chloride 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 以95%的产率得到cis-(Z)-α-(1-chloroethylidene)-γ-isopropyl-β-vinyl-γ-butyrolactone
  参考文献：
  名称：

  Controlling factors on the stereochemistry of palladium(II)-catalyzed cyclization of 1'-alkyl-4'-chloro-2'-alkenyl 2-alkynoates

  摘要：

  Beta,gamma-Disubstituted alpha-(Z)-(chloromethylene)-gamma-butyrolactone derivatives have been prepared highly diastereoselectively via a Pd(II)-catalyzed cyclization of 1'-alkyl-4'-chloro-2'-alkenyl 2-alkynoates. Rationales for the stereochemical results of this reaction are proposed.

  DOI：

  10.1021/jo00066a022
• 作为产物：
  描述：

  5-methyl-2(E)-hexene-1,4-diol 在 2,4,6-三甲基吡啶 、 4-二甲氨基吡啶 、 甲基磺酰氯 、 N,N'-二环己基碳二亚胺 、 lithium chloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 1'-isopropyl-4'-chloro-2'(E)-butenyl 2-butenoate
  参考文献：
  名称：

  Controlling factors on the stereochemistry of palladium(II)-catalyzed cyclization of 1'-alkyl-4'-chloro-2'-alkenyl 2-alkynoates

  摘要：

  Beta,gamma-Disubstituted alpha-(Z)-(chloromethylene)-gamma-butyrolactone derivatives have been prepared highly diastereoselectively via a Pd(II)-catalyzed cyclization of 1'-alkyl-4'-chloro-2'-alkenyl 2-alkynoates. Rationales for the stereochemical results of this reaction are proposed.

  DOI：

  10.1021/jo00066a022

文献信息

• Palladium-Catalyzed Tandem Cyclization/Suzuki Coupling of 1,6-Enynes:  Reaction Scope and Mechanism
  作者：Gangguo Zhu、Xiaofeng Tong、Jiang Cheng、Yanhui Sun、Dao Li、Zhaoguo Zhang

  DOI：10.1021/jo048238j

  日期：2005.3.1

  A palldium(0)-catalyzed tandem cyclization/Suzuki coupling reaction of various 1,6-enyne substrates was developed. This Pd-catalyzed enyne cyclization reaction represents a new process for the synthesis of stereodefined α-arylmethylene-γ-butyrolactones, lactams, multifunctional tetrahydrofurans, pyrrolidines, and cyclopentanes. The mechanism of the reaction was studied by the employment of different

  开发了钯（0）催化的各种1,6-烯炔底物的串联环化/ Suzuki偶联反应。这种Pd催化的烯炔环化反应代表了合成立体定义的α-芳基亚甲基-γ-丁内酯，内酰胺，多功能四氢呋喃，吡咯烷和环戊烷的新方法。通过使用不同的烯炔异构体和硼酸研究了反应机理。建议使用π-烯丙基钯中间体来解释环状产物的形成。该反应的立体化学可以通过椅子状过渡态很好地解释。
• Zhu, Guoxin; Ma, Shengming; Lu, Xiyan, Journal of Chemical Research, Miniprint, 1993, # 9, p. 2467 - 2480
  作者：Zhu, Guoxin、Ma, Shengming、Lu, Xiyan

  DOI：——

  日期：——
• Ma Shengming, Zhu Guoxin, Lu Xiyan, J. Org. Chem., 58 (1993) N 14, S 3692-3696
  作者：Ma Shengming, Zhu Guoxin, Lu Xiyan

  DOI：——

  日期：——
• Controlling factors on the stereochemistry of palladium(II)-catalyzed cyclization of 1'-alkyl-4'-chloro-2'-alkenyl 2-alkynoates
  作者：Shengming Ma、Guoxin Zhu、Xiyan Lu

  DOI：10.1021/jo00066a022

  日期：1993.7

  Beta,gamma-Disubstituted alpha-(Z)-(chloromethylene)-gamma-butyrolactone derivatives have been prepared highly diastereoselectively via a Pd(II)-catalyzed cyclization of 1'-alkyl-4'-chloro-2'-alkenyl 2-alkynoates. Rationales for the stereochemical results of this reaction are proposed.