(3R,4R)-3-methyl-4-(3-oxobutyl)cyclopentan-1-one | 127379-63-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4R)-3-methyl-4-(3-oxobutyl)cyclopentan-1-one
• CAS: 127379-63-9
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: PLFPEYANYWRYLU-VXNVDRBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (3R,4R)-3-methyl-4-(3-oxobutyl)cyclopentan-1-one 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 以60%的产率得到(3R,3aS,6aR)-3,6-Dimethyl-3,3a,4,6a-tetrahydro-2H-pentalen-1-one
  参考文献：
  名称：

  Stereoselective Construction of the Dicyclopenta[a,d]cyclooctene Core of the Ceroplastin Sesterterpenes by Way of the Anionic Oxy-Cope Rearrangement

  摘要：

  Bicyclo[3.2.1]octanediones such as 9, which are readily available by double carbonylation of (1,3-cyclohexadiene)iron tricarbonyl complexes according to Eilbracht, are amenable to regiospecific methylenation under Wittig conditions. Reduction of 10 with copper hydride leads to 11, which can be resolved by application of Johnson's sulfoximine technology and oxidized to give the enantiopure antipodes of 10. Variously substituted cyclopentenyl anions undergo 1,2-addition to 10, providing carbinols which are capable of anionic oxy-Cope rearrangement via chair transition states. These structural reorganizations are fully stereocontrolled and lead directly to functionalized dicyclopenta[a,d]cyclooctenes. When 11 is treated analogously, only [1,3] sigmatropy is observed and inversion of stereochemistry at the migrating carbon prevails. Both processes exhibit impressive scaffolding powers and are characterized by brevity.

  DOI：

  10.1021/jo952165+
• 作为产物：
  描述：

  (R)-6-oxo-3-(prop-1-en-2-yl)heptanal 在 chlorobis(cyclooctene)rhodium(I) dimer 、 (+)-DIPMC 作用下， 以 二氯甲烷 为溶剂， 生成 (3R,4R)-3-methyl-4-(3-oxobutyl)cyclopentan-1-one 、 (3S,4R)-3-methyl-4-(3-oxobutyl)cyclopentan-1-one
  参考文献：
  名称：

  不对称环化反应。带有手性配体的铑（I）将取代的4-戊烯环化为环戊酮衍生物

  摘要：

  测试了Rh（I）与手性配体对取代的4-戊烯（Ia，b，c; IIa，b，c，d）的不对称环化作用，并在C 4处具有更大取代基的底物（IId）通过Rh（I）-（（+）-DIPMC）生成取代的环戊酮（IIID）。发现具有（+）-DIPMC的Rh（I）以不同于威尔金森催化的环化的方式进行。

  DOI：

  10.1016/s0040-4020(01)80954-6

文献信息

• Highly enantioselective cyclization using cationic Rh(I) with chiral ligand
  作者：Xiao-Ming Wu、Kazuhisa Funakoshi、Kiyoshi Sakai

  DOI：10.1016/s0040-4039(00)60966-8

  日期：1992.10

  (>99% de) of 3R (or S) 3,4-disubstituted 4-pentenals into the corresponding 3,4-cis(or trans)-disubstituted cyclopentanone and highly enantioselective cyclization (>99% ee) of 4-substituted 4-pentenals into 3-substituted cyclopentanone were achieved by using cationic Rh+(BINAP)ClO4−.

  3R（或S）3,4-二取代的4-戊烯的非对映选择性环化（> 99％de）转化为相应的3,4-顺（或反式）-二取代的环戊酮和4的高度对映选择性环化（> 99％ee） -取代的4-戊烯醛为3-取代环戊酮通过使用阳离子铑达到+（BINAP）CLO 4 - 。
• TAURA, YUKARI;TANAKA, MASAKAZU;FUNAKOSHI, KAZUHISA;SAKAI, KIYOSHI, TETRAHEDRON LETT., 30,(1989) N6, C. 6349-6352
  作者：TAURA, YUKARI、TANAKA, MASAKAZU、FUNAKOSHI, KAZUHISA、SAKAI, KIYOSHI

  DOI：——

  日期：——