methyl (E)-3-[(2R)-2-(3-methoxypentan-3-yl)pyrrolidin-1-yl]-4-(2-trimethylsilylethoxy)but-2-enoate | 222052-49-5

• 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: methyl (E)-3-[(2R)-2-(3-methoxypentan-3-yl)pyrrolidin-1-yl]-4-(2-trimethylsilylethoxy)but-2-enoate
• CAS: 222052-49-5
• 化学式: C₂₀H₃₉NO₄Si
• 分子量: 385.619
• InChiKey: OZRRCQARWIBNIO-WBWKYDSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-[(2R)-2-(3-methoxypentan-3-yl)pyrrolidin-1-yl]-4-(2-trimethylsilylethoxy)but-2-enoate 在 sodium cyanoborohydride 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3S)-2-[(E)-prop-1-enyl]-3-(2-trimethylsilylethoxy)-2,3-dihydropyran-6-one
  参考文献：
  名称：

  Asymmetric total synthesis of (+)-phomalactone, (+)-acetylphomalactone and (+)-asperlin utilizing a novel syn-selective C4-oxa-vinylogous urethane

  摘要：

  The total synthesis of three natural products isolated from Nigrospora sp., Phoma sp., and Aspergillus nidulans(l) starting from an aldol reaction with a homochiral C-4-oxa-vinylogous urethane is described. Inherent stereoselectivity of the aldol reaction and overall alacrity of molecular construction are discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02675-6
• 作为产物：
  描述：

  7,7-dimethyl-4-oxa-7-sila-1-octyne 在 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 methyl (E)-3-[(2R)-2-(3-methoxypentan-3-yl)pyrrolidin-1-yl]-4-(2-trimethylsilylethoxy)but-2-enoate
  参考文献：
  名称：

  Asymmetric total synthesis of (+)-phomalactone, (+)-acetylphomalactone and (+)-asperlin utilizing a novel syn-selective C4-oxa-vinylogous urethane

  摘要：

  The total synthesis of three natural products isolated from Nigrospora sp., Phoma sp., and Aspergillus nidulans(l) starting from an aldol reaction with a homochiral C-4-oxa-vinylogous urethane is described. Inherent stereoselectivity of the aldol reaction and overall alacrity of molecular construction are discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02675-6

文献信息

• Asymmetric total synthesis of (+)-phomalactone, (+)-acetylphomalactone and (+)-asperlin utilizing a novel syn-selective C4-oxa-vinylogous urethane
  作者：Richard H. Schlessinger、Kevin W. Gillman

  DOI：10.1016/s0040-4039(98)02675-6

  日期：1999.2

  The total synthesis of three natural products isolated from Nigrospora sp., Phoma sp., and Aspergillus nidulans(l) starting from an aldol reaction with a homochiral C-4-oxa-vinylogous urethane is described. Inherent stereoselectivity of the aldol reaction and overall alacrity of molecular construction are discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.