(1S,4R)-(+)-4-(tert-butyldimethylsilanyloxymethyl)cyclopent-2-enol | 144938-70-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (1S,4R)-(+)-4-(tert-butyldimethylsilanyloxymethyl)cyclopent-2-enol
• 英文别名: cis-(1S,4R)-4-tert-butyldimethylsilyloxymethyl-2-cyclopenten-1-ol；(1S,4R)-cis-4-tert-butyldimethylsiloxymethyl-2-cyclopenten-1-ol；(1S,4R)-(+)-4-(tert-Butyldimethylsiloxymethyl)cyclopent-2-enol；(1S,4R)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclopent-2-en-1-ol
• CAS: 144938-70-5
• 化学式: C₁₂H₂₄O₂Si
• 分子量: 228.407
• InChiKey: REQFKGQMIDQOOU-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,4R)-(+)-4-(tert-butyldimethylsilanyloxymethyl)cyclopent-2-enol 在 N-溴代丁二酰亚胺(NBS) 、 二苯甲酮 、 四丁基氟化铵 、 六甲基二锡 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 23.0h， 生成 (3RS,4aS,7aR)-1,3,4,4a-hexahydro-cyclopenta[c]pyran-3-ol
  参考文献：
  名称：

  Enantioselective synthesis of cis-1,2-dialkyl substituted cyclopentanoid and isoprostane building blocks via 6-exo-trigonal radical cyclizations

  摘要：

  Two different 6-exo-trigonal cyclizations of enantiomerically enriched 6-heptenyl radicals readily afforded versatile synthetic precursors of cis-1,2-dialkyl substituted cyclopentane derivatives. Starting from one of these intermediates, we accomplished an enantiospecific formal synthesis of two important isoprostanes, namely 15-F-2c-IsoP and ent-15-F-2c-IsoP. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00312-3
• 作为产物：
  描述：

  cis-(1R,4S)-4-tert-butyldimethylsilyloxymethyl-2-cyclopenten-1-ol 在 吡啶 、 4-二甲氨基吡啶 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 生成 (1S,4R)-(+)-4-(tert-butyldimethylsilanyloxymethyl)cyclopent-2-enol
  参考文献：
  名称：

  Shoberu, Karoline A.; Roberts, Stanley M., Journal of the Chemical Society. Perkin transactions I, 1992, # 18, p. 2419 - 2426

  摘要：

  DOI：

文献信息

• Synthesis of chiral non-racemic 1,2-diamines from O-acetyl mandelic acid: application in enantioselective deprotonation of epoxides and diethylzinc addition to aldehydes
  作者：P Saravanan、Alakesh Bisai、S Baktharaman、M Chandrasekhar、Vinod K Singh

  DOI：10.1016/s0040-4020(02)00376-9

  日期：2002.6

  A variety of 1,2-diamines were synthesized from readily available O-acetyl mandelic acid. These diamines were used in the synthesis of key intermediates for the preparation of (-)-utenone A and carbovir involving enantioselective deprotonation of epoxides, The addition of Et2Zn catalysed by some of these diamines was also studied and although ees were not high, some interesting observations were made in the outcome of the stereochemistry of the product. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Roberts, Stanley M.; Shoberu, Karoline A., Journal of the Chemical Society. Perkin transactions I, 1991, # 4, p. 2605 - 2607
  作者：Roberts, Stanley M.、Shoberu, Karoline A.

  DOI：——

  日期：——
• An asymmetric synthesis of (−)-carbovir
  作者：Masatoshi Asami、Jun Takahashi、Seiichi Inoue

  DOI：10.1016/0957-4166(94)80072-3

  日期：1994.9

  Enantioselective deprotonation of trans-4-t-butyldimethylsiloxymethyl-1,2-epoxycyclopentane (trans-4) by a chiral lithium amide, lithium (S)-2-(pyrrolidin-1-ylmethyl)pyrrolidide (1), afforded (1S,4S)-trans-4-t-butyldimethylsiloxymethyl-2-cyclopenten-1-ol (trans-7) in 83 %ee. Alcohol trans-7 was easily transformed to (-)-carbovir, an anti-HIV carbocyclic nucleoside.