(1RS,7SR)-bicyclo[5.1.0]octan-2-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1RS,7SR)-bicyclo[5.1.0]octan-2-one
• 英文别名: (1R,7S)-bicyclo[5.1.0]octan-2-one
• 化学式: C₈H₁₂O
• 分子量: 124.183
• InChiKey: AKDQJROTPGHKES-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1RS,7SR)-bicyclo[5.1.0]octan-2-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 89.0h， 生成 (1S*,3S*,7R*)-3-(2-methyl-2-propenyl)-3-methylbicyclo[5.1.0]octan-2-one
  参考文献：
  名称：

  Diastereoselective Manipulations of Bicyclo[m.1.0]alkane Derivatives. 6. Stereocontrolled Synthesis of Tricyclo[m.n.0.0]alkenones

  摘要：

  Enolates derived from bicyclo[m.1.0]alkan-2-ones possessing 5-, 6-, and 7-membered rings were sequentially alkylated with iodomethane and with precursors to 2-oxopropyl or 3-oxobutyl substituents. High diastereoselectivities were observed. Product yields for more active electrophiles were generally good to very good and were fair for less active electrophiles. Following unmasking of the 2-oxopropyl or 3-oxobutyl substituents, ring closure and dehydration under basic conditions provided the corresponding tricyclic gamma,delta-cyclopropyl-alpha,beta-enones. Reversal of the order of alkylation switched the configuration of the angular methyl substituent relative to the stereogenic cyclopropane in the tricyclo[m.n.0.0]alkenone product.

  DOI：

  10.1021/jo990720s
• 作为产物：
  描述：

  2-环庚烯-1-酮 在 锌铜偶 、 硫酸 、 碘 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.5h， 生成 (1RS,7SR)-bicyclo[5.1.0]octan-2-one
  参考文献：
  名称：

  Homochiral ketals in organic synthesis. Diastereoselective cyclopropanation

  摘要：

  DOI：

  10.1021/ja00312a073

文献信息

• Diastereoselective Manipulations of Bicyclo[<i>m</i>.1.0]alkane Derivatives. 2. Nucleophilic Additions to the Carbonyl Carbons of Bicyclo[<i>m</i>.1.0]alkan-2-ones¹
  作者：Eugene A. Mash、Timothy M. Gregg、Michelle A. Kaczynski

  DOI：10.1021/jo951753k

  日期：1996.1.1

  Enantiomerically enriched bicyclo[m.1.0]alkan-2-ones having larger ring sizes between five and 16 members were prepared and subjected to additions of nucleophiles to the carbonyl carbon. Such additions were efficient and highly diastereoselective for all nucleophiles for bicycles with ring sizes greater than seven. Diastereoselectivity for these additions is rationalized by assuming early transition states and exposure of the same carbonyl face to the ring exterior in the vast majority of populated conformers for each bicyclic ketone.
• Diastereoselective manipulations of conformationally restricted enantiomerically pure bicyclo[m.1.0]alkanes. 1. Nucleophilic additions to the carbonyl carbons of bicyclo[m.1.0]alkan-2-ones
  作者：Eugene A. Mash、Michelle A. Kaczynski、Daniel P. Dolata

  DOI：10.1016/s0040-4039(00)97677-9

  日期：1990.1
• Diastereoselective manipulations of bicyclo[m.1.0]alkane derivatives. 5. α′-alkylations of bicyclo[m.1.0]alkan-2-ones
  作者：Eugene A. Mash、James A. Baron、Timothy M. Gregg、Sandeep K. Nimkar

  DOI：10.1016/s0040-4020(98)83003-2

  日期：1998.3

  alpha'-Alkylations of bicyclo[m.1.0]alkan-2-ones were shown to proceed with high diastereoselectivity under conditions which favor kinetic control of the product distribution. Product yields for active electrophiles were good to very good. In sequential alpha'-alkylations with different electrophiles, reversal of the order of alkylation switches the configuration of the newly formed quaternary center. (C) 1998 Elsevier Science Ltd. All rights reserved.
• MASH, EUGENE A.;KACZYNSKI, MICHELLE A.;DOLATA, DANIEL P., TETRAHEDRON LETT., 31,(1990) N2, C. 4565-4568
  作者：MASH, EUGENE A.、KACZYNSKI, MICHELLE A.、DOLATA, DANIEL P.

  DOI：——

  日期：——
• MASH, E. A.;NELSON, K. A., J. AMER. CHEM. SOC., 1985, 107, N 26, 8256-8258
  作者：MASH, E. A.、NELSON, K. A.

  DOI：——

  日期：——