tert-butyl N-[(1S,2R)-2-[(2R)-1-hydroxypropan-2-yl]-1-prop-2-enylcyclopentyl]carbamate | 250595-68-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: tert-butyl N-[(1S,2R)-2-[(2R)-1-hydroxypropan-2-yl]-1-prop-2-enylcyclopentyl]carbamate
• CAS: 250595-68-7
• 化学式: C₁₆H₂₉NO₃
• 分子量: 283.411
• InChiKey: HILOTQZPIIPLGW-WOSRLPQWSA-N

物化性质

• 沸点：
  388.2±11.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(1S,2R)-2-[(2R)-1-hydroxypropan-2-yl]-1-prop-2-enylcyclopentyl]carbamate 在 4-二甲氨基吡啶 、 9-borabicyclo[3.3.1]nonane dimer 、 水 、 potassium carbonate 、 三乙胺 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 生成 tert-butyl (2'R,6S,9aR)-2'-[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]-2-oxospiro[3,4,7,8,9,9a-hexahydro-1H-quinolizine-6,1'-cyclopentane]-3-carboxylate
  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：

  (R)-2-((1R,2S)-2-Allyl-2-tert-butoxycarbonylamino-cyclopentyl)-propionic acid 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 tert-butyl N-[(1S,2R)-2-[(2R)-1-hydroxypropan-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

文献信息

• Studies towards the total synthesis of halichlorine: asymmetric synthesis of the spiroquinolizidine subunit
  作者：Dirk Trauner、Samuel J Danishefsky

  DOI：10.1016/s0040-4039(99)01170-3

  日期：1999.9

  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.
• 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.
  作者：Matthew W. Carson、Guncheol Kim、Martin F. Hentemann、Dirk Trauner、Samuel J. Danishefsky

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

  日期：2001.12.3
• 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.