(1R)-cis-10-isopropyl-7-methyl-cis-1-transoid-1,2-cis-2-tricyclo<5.3.0.0^2,6>decane-3-one | 13844-03-6

• 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: (1R)-cis-10-isopropyl-7-methyl-cis-1-transoid-1,2-cis-2-tricyclo<5.3.0.0^2,6>decane-3-one
• 英文别名: 11-norbourbonan-1-one；(-)-norbourbonene；(-)-norbourbonone；1-norbourbonanone；norbourbonone；2-Methyl-5-isopropyl-tricyclo<5.3.0.0.^2,6>decan-8-on；(1R,2S,6R,7S,10S)-7-methyl-10-propan-2-yltricyclo[5.3.0.02,6]decan-3-one
• CAS: 13844-03-6
• 化学式: C₁₄H₂₂O
• 分子量: 206.328
• InChiKey: PYUWACLOPFTHBV-HNTFPEDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  (1R)-cis-10-isopropyl-7-methyl-cis-1-transoid-1,2-cis-2-tricyclo<5.3.0.0^2,6>decane-3-one 生成 β-(1-Methyl-4-isopropylbicyclo<3.2.0>hept-6-en-7-yl)propanal
  参考文献：
  名称：

  The absolute stereostructure of α- and β-bourbonene, sesquiterpenic hydrocarbons from the essential oil geranium bourbon

  摘要：

  DOI：

  10.1016/s0040-4039(01)99939-3
• 作为产物：
  描述：

  (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 在 吡啶 、 盐酸 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 生成 (1R)-cis-10-isopropyl-7-methyl-cis-1-transoid-1,2-cis-2-tricyclo<5.3.0.0^2,6>decane-3-one
  参考文献：
  名称：

  以γ-羟甲基-γ-丁内酯为手性合成子的顺式，反式，顺式-三环[5,3,0,0 2,6 ]癸烷的不对称合成。（-）-β-波旁烯的首次不对称全合成

  摘要：

  描述了顺式，反式，顺式-三环[5,3,0,0 2,6 ]癸烷倍半萜烯β-波本烯的不对称全合成。使用光学纯的丁烯内酯衍生物6b作为手性合成子进行关键的（2 + 2）光环加成。

  DOI：

  10.1016/s0040-4039(00)87626-1

文献信息

• Stereospecific Synthesis of 3-Oxo-α-bourbonene and the Cisoid Isomer for Structural Determination of the Toxic Component of<i>Lansium domesticum</i>
  作者：Tadao Uyehara、Ichiro Suzuki、Yoshinori Yamamoto

  DOI：10.1246/bcsj.61.2672

  日期：1988.7

  The cis-cisoid-cis isomer of 3-oxo-α-bourbonene, (1), the original structure proposed for the toxic principle of Lansium domesticum, has been prepared from (−)-mintsulfide. Neither spectral data of 1 nor of 3-oxo-α-bourbonene itself, derived from β-bourbonene, are not identical with those of the toxic componet.

  3-氧代-α-波旁烯的顺式-顺式-顺式异构体（1）是为家养兰的毒性原理提出的原始结构，已从（-）-薄荷硫化物制备。1 和衍生自 β-波旁烯的 3-氧代-α-波旁烯本身的光谱数据都与有毒成分的光谱数据不同。
• Tomioka, Kiyoshi; Tanaka, Masahide; Koga, Kenji, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 5, p. 1201 - 1207
  作者：Tomioka, Kiyoshi、Tanaka, Masahide、Koga, Kenji

  DOI：——

  日期：——
• A short enantiospecific route to isodaucane sesquiterpenes from limonene. On the absolute configuration of (+)-aphanamol I and II.
  作者：Thomas Hansson、Boerje Wickberg

  DOI：10.1021/jo00046a018

  日期：1992.9

  The isodaucane sesquiterpenes (+)-aphanamol I (3) and (-)-2-oxoisodauc-5-en-12-al [(-)-6] have been prepared in a short reaction sequence from 5(S)-isopropyl-2-methyl-l-cyclopentene-1-carbaldehyde (S)-23 (readily obtainable from (+)-limonene). Key steps were a de Mayo type photocyclization of an 3-acyloxy-2-cyclopenten-1-one with 3(S)-isopropyl-1-methylcyclopentene [(S)-24] to a [5.3.0.0(2.6)]tricyclodecanone (e.g., (-)-28) with the desired configuration at all stereocenters and the formation of 3 by a base-catalyzed fragmentation of the gamma,delta-epoxyalcohol intermediate 33 (R = H), which produced all the desired functional groups in one step. The stereochemical assignments were supported by CD data as well as by the synthesis of (-)-norbourbonone (29) from (S)-24, which is a novel chiral intermediate. These results are in confliction with some earlier assignmnents of the absolute configuration in the isodaucane group of sesquiterpenes.
• The structure and absolute configuration of α- and β-bourbonene, sesquiterpenic hydrocarbons from the essential oil of geranium bourbon
  作者：J. Křepinský、Z. Samek、F. Šorm、D. Lamparsky、. Ochsner、Y.-R. Naves

  DOI：10.1016/s0040-4020(01)82169-4

  日期：1966.1
• TOMIOKA, KIYOSHI;TANAKA, MASAHIDE;KOGA, KENJI, CHEM. AND PHARM. BULL., 37,(1989) N, C. 1201-1207
  作者：TOMIOKA, KIYOSHI、TANAKA, MASAHIDE、KOGA, KENJI

  DOI：——

  日期：——