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(3R,4R)-3-formylmethyl-3-isopropenyl-4-methylcyclopentanone | 315195-13-2

中文名称
——
中文别名
——
英文名称
(3R,4R)-3-formylmethyl-3-isopropenyl-4-methylcyclopentanone
英文别名
2-[(1R,2R)-2-methyl-4-oxo-1-prop-1-en-2-ylcyclopentyl]acetaldehyde
(3R,4R)-3-formylmethyl-3-isopropenyl-4-methylcyclopentanone化学式
CAS
315195-13-2
化学式
C11H16O2
mdl
——
分子量
180.247
InChiKey
WYTNGECXMLGWRC-KOLCDFICSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    1.4
  • 重原子数:
    13
  • 可旋转键数:
    3
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.64
  • 拓扑面积:
    34.1
  • 氢给体数:
    0
  • 氢受体数:
    2

反应信息

  • 作为反应物:
    描述:
    (3R,4R)-3-formylmethyl-3-isopropenyl-4-methylcyclopentanone 在 Rh(I)Cl(R-BINAP) 作用下, 以 二氯甲烷 为溶剂, 生成 (3R,4R)-3,4-dimethyl-3-isopropenylcyclopentanone
    参考文献:
    名称:
    Application of Rh-catalyzed cyclization for the construction of three consecutive chiral carbons in 4,9-dimethylspiro[4.4]nonane-2,7-dione
    摘要:
    Asymmetric cyclization using Rh-complexes has been applied to the synthesis of 4,9-dimethylspiro[4.4]nonane-2,7-diones. The spiro[4.4]nonane skeleton bearing three consecutive chiral carbons could be stepwisely constructed from an identical starting material by the combination of a cationic Rh[(S)BINAP]ClO4 and a neutral RhCl(PPh3)(3). The relationship between the stereochemistry of the spirodiketones and the Rh-complex was also discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.
    DOI:
    10.1016/s0040-4039(00)01315-0
  • 作为产物:
    描述:
    (3R,4R)-3-isopropenyl-3-(2-hydroxyethyl)-4-methylcyclopentanone 在 sodium acetatepyridinium chlorochromate 作用下, 以 二氯甲烷 为溶剂, 生成 (3R,4R)-3-formylmethyl-3-isopropenyl-4-methylcyclopentanone
    参考文献:
    名称:
    Enantio- and diastereoselective construction of 4,9-dimethylspiro[4.4]nonane-2,7-dione using Rh-catalyzed asymmetric cyclization
    摘要:
    Asymmetric cyclization using Rh-complexes was applied to the synthesis of 4,9-dimethylspiro[4.4]nonane-2,7-diones. The spiro[4.4]nonane skeleton bearing a chiral quaternary carbon could be stepwisely constructed by using Rh-catalyzed cyclization twice. All diastereomers of the spirodiketone could be stereoselectively prepared from the identical starting material by the combination of a neutral Rh(PPh3)(3)Cl and a cationic Rh[BINAP]ClO4. The cyclization by the neutral Rh(PPh3)(3)Cl proceeded to give cis-3,4-disubstituted cyclopentanones, while that by the cationic Rh[BINAP]ClO4 proceeded to afford trans-3,4-disubstituted cyclopentanones. Four spirodiketones of six stereoisomers could be prepared in optically active form, and the relationship between the stereochemistry of the spirodiketones and the Rh-complex was discussed based on the plausible acyl-hydride Rh-complexes. (C) 2001 Elsevier Science Ltd. All rights reserved.
    DOI:
    10.1016/s0040-4020(00)01106-6
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文献信息

  • Application of Rh-catalyzed cyclization for the construction of three consecutive chiral carbons in 4,9-dimethylspiro[4.4]nonane-2,7-dione
    作者:Miyuki Takahashi、Masakazu Tanaka*、Eishi Sakamoto、Masanori Imai、Akiko Matsui、Kazuhisa Funakoshi、Kiyoshi Sakai、Hiroshi Suemune
    DOI:10.1016/s0040-4039(00)01315-0
    日期:2000.10
    Asymmetric cyclization using Rh-complexes has been applied to the synthesis of 4,9-dimethylspiro[4.4]nonane-2,7-diones. The spiro[4.4]nonane skeleton bearing three consecutive chiral carbons could be stepwisely constructed from an identical starting material by the combination of a cationic Rh[(S)BINAP]ClO4 and a neutral RhCl(PPh3)(3). The relationship between the stereochemistry of the spirodiketones and the Rh-complex was also discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.
  • Enantio- and diastereoselective construction of 4,9-dimethylspiro[4.4]nonane-2,7-dione using Rh-catalyzed asymmetric cyclization
    作者:Masakazu Tanaka、Miyuki Takahashi、Eishi Sakamoto、Masanori Imai、Akiko Matsui、Masakazu Fujio、Kazuhisa Funakoshi、Kiyoshi Sakai、Hiroshi Suemune
    DOI:10.1016/s0040-4020(00)01106-6
    日期:2001.2
    Asymmetric cyclization using Rh-complexes was applied to the synthesis of 4,9-dimethylspiro[4.4]nonane-2,7-diones. The spiro[4.4]nonane skeleton bearing a chiral quaternary carbon could be stepwisely constructed by using Rh-catalyzed cyclization twice. All diastereomers of the spirodiketone could be stereoselectively prepared from the identical starting material by the combination of a neutral Rh(PPh3)(3)Cl and a cationic Rh[BINAP]ClO4. The cyclization by the neutral Rh(PPh3)(3)Cl proceeded to give cis-3,4-disubstituted cyclopentanones, while that by the cationic Rh[BINAP]ClO4 proceeded to afford trans-3,4-disubstituted cyclopentanones. Four spirodiketones of six stereoisomers could be prepared in optically active form, and the relationship between the stereochemistry of the spirodiketones and the Rh-complex was discussed based on the plausible acyl-hydride Rh-complexes. (C) 2001 Elsevier Science Ltd. All rights reserved.
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