methyl 7-[(3R)-3-[tert-butyl(dimethyl)silyl]oxy-5-oxocyclopenten-1-yl]hept-2-ynoate | 131392-91-1

• 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 7-[(3R)-3-[tert-butyl(dimethyl)silyl]oxy-5-oxocyclopenten-1-yl]hept-2-ynoate
• CAS: 131392-91-1
• 化学式: C₁₉H₃₀O₄Si
• 分子量: 350.53
• InChiKey: RQCJULULRVPMSY-INIZCTEOSA-N

物化性质

• 沸点：
  435.8±45.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (3S,4R)-4-[tert-butyl(dimethyl)silyl]oxy-3-methoxy-2-methylidenecyclopentan-1-one 在 偶氮二异丁腈 、 tributylstannyllithium 作用下， 反应 3.0h， 生成 methyl 7-[(3R)-3-[tert-butyl(dimethyl)silyl]oxy-5-oxocyclopenten-1-yl]hept-2-ynoate
  参考文献：
  名称：

  Radical Addition Reactions to Allylstannanes Having Substituents at C-1. Highly Efficient Synthesis of Enantiomerically Pure .alpha.-Alkylcyclopentenones, the Key Component for Synthesis of Prostaglandins by the Two-Component Coupling Process

  摘要：

  A highly efficient and practical method for the synthesis of enantiomerically pure 4-alkoxy-2-alkyl-2-cyclopenten-1-ones 1, the key component for the preparation of prostaglandins via the two-component coupling process, has been developed. The method involves the preparation of 4-alkoxy-2-methylene-3-(tributylstannyl) cyclopentan-1-one 6 from readily available 4-alkoxy-2-[(diethylamino)methyl]-2-cyclopenten-1-one 5 and its reaction with alkyl radicals.

  DOI：

  10.1021/jo00100a010

文献信息

• A highly practical synthesis of natural PGE1, Δ2-trans-PGE1 and 2,2,3,3-tetradehydro-PGE1 via two-component coupling process using zinc-copper reagents
  作者：Hiromi Tsujiyama、Naoya Ono、Toshiharu Yoshino、Sentaro Okamoto、Fumie Sato

  DOI：10.1016/s0040-4039(00)97654-8

  日期：1990.1
• TSUJIYAMA, HIROMI;ONO, NAOYA;YOSHINO, TOSHIHARU;OKAMOTO, SENTARO, TETRAHEDRON LETT., 31,(1990) N1, C. 4481-4484
  作者：TSUJIYAMA, HIROMI、ONO, NAOYA、YOSHINO, TOSHIHARU、OKAMOTO, SENTARO

  DOI：——

  日期：——
• Radical Addition Reactions to Allylstannanes Having Substituents at C-1. Highly Efficient Synthesis of Enantiomerically Pure .alpha.-Alkylcyclopentenones, the Key Component for Synthesis of Prostaglandins by the Two-Component Coupling Process
  作者：Yukio Yoshida、Naoya Ono、Fumie Sato

  DOI：10.1021/jo00100a010

  日期：1994.10

  A highly efficient and practical method for the synthesis of enantiomerically pure 4-alkoxy-2-alkyl-2-cyclopenten-1-ones 1, the key component for the preparation of prostaglandins via the two-component coupling process, has been developed. The method involves the preparation of 4-alkoxy-2-methylene-3-(tributylstannyl) cyclopentan-1-one 6 from readily available 4-alkoxy-2-[(diethylamino)methyl]-2-cyclopenten-1-one 5 and its reaction with alkyl radicals.