tert-butyl (3R,3aR,6aS)-3-methyl-2-oxo-6a-prop-2-enyl-3a,4,5,6-tetrahydro-3H-cyclopenta[b]pyrrole-1-carboxylate | 250595-66-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl (3R,3aR,6aS)-3-methyl-2-oxo-6a-prop-2-enyl-3a,4,5,6-tetrahydro-3H-cyclopenta[b]pyrrole-1-carboxylate
• CAS: 250595-66-5
• 化学式: C₁₆H₂₅NO₃
• 分子量: 279.379
• InChiKey: GVINAZWKCOVGGC-XHBSWPGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (3R,3aR,6aS)-3-methyl-2-oxo-6a-prop-2-enyl-3a,4,5,6-tetrahydro-3H-cyclopenta[b]pyrrole-1-carboxylate 在 4-二甲氨基吡啶 、 lithium hydroxide 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 tert-butyl N-[(1S,2R)-2-[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]-1-prop-2-enylcyclopentyl]carbamate
  参考文献：
  名称：

  Studies towards the total synthesis of halichlorine: asymmetric synthesis of the spiroquinolizidine subunit

  摘要：

  The C1-C15 spiroquinolizidine subunit (cf. 2) of the marine natural product halichlorine (1) was prepared in 12 steps starting from the known 'Meyers-lactam' 5. The synthesis involves a B-alkyl-Suzuki coupling followed by a highly stereoselective intramolecular Michael addition and an intramolecular Mannich ring closure. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01170-3
• 作为产物：
  描述：

  (3aR,6aS)-6a-prop-2-enyl-1,3,3a,4,5,6-hexahydrocyclopenta[b]pyrrol-2-one 在 4-二甲氨基吡啶 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 19.0h， 生成 tert-butyl (3R,3aR,6aS)-3-methyl-2-oxo-6a-prop-2-enyl-3a,4,5,6-tetrahydro-3H-cyclopenta[b]pyrrole-1-carboxylate
  参考文献：
  名称：

  Concise Stereoselective Routes to Advanced Intermediates Related to Natural and Unnatural Pinnaic Acid This work was supported by the National Institutes of Health (Grant Numbers: CA28824). Postdoctoral Fellowship support is gratefully acknowledged by M.W.C. (U.S. Army BCRP, DAMD17-98-1-8154), M.F.H. (5T32 CA62948-05), and D.T. (Schering Research Foundation, Berlin). We thank Dr. George Sukenick of the MSKCC NMR Core Facility for NMR and mass spectral analyses.

  摘要：

  DOI：

  10.1002/1521-3773(20011203)40:23<4450::aid-anie4450>3.0.co;2-m

文献信息

• Total Synthesis of (+)-Halichlorine: An Inhibitor of VCAM-1 Expression
  作者：Dirk Trauner、Jacob B. Schwarz、Samuel J. Danishefsky

  DOI：10.1002/(sici)1521-3773(19991203)38:23<3542::aid-anie3542>3.0.co;2-i

  日期：——

  The diastereoselective addition of the highly functionalized organozinc compound 1 to the aldehyde 2 in the presence of the chiral amino alcohol 3 (-->4) is a key step in the first total synthesis of (+)-halichlorine. A series of protections/deprotections and a macrolaconization complete the synthesis. Halichlorine selectively inhibits the expression of the cell adhesion molecule VCAM-1. TBS=tert-butyldimethylsilyl.