bicyclo[7.3.1]tridec-12-en-11-one | 111077-48-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: bicyclo[7.3.1]tridec-12-en-11-one
• 英文别名: Bicyclo[7.3.1]tridec-9-en-11-one；bicyclo[7.3.1]tridec-1(12)-en-11-one
• CAS: 111077-48-6
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: RXVUBPIPKJMTSR-UHFFFAOYSA-N

物化性质

• 沸点：
  323.7±9.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  bicyclo[7.3.1]tridec-12-en-11-one 在 hematoporphyrin 氧气 作用下， 以 丙酮 为溶剂， 以89%的产率得到14,15-Dioxa-tricyclo[10.3.1.04,13]hexadeca-3,12(16)-dien-2-one
  参考文献：
  名称：

  [7]- and [9](3,5)troponophanes and the corresponding hydroxytropyliophanes

  摘要：

  DOI：

  10.1016/s0040-4039(00)95788-5
• 作为产物：
  描述：

  trans-2-cyclodecen-1-one 、 乙酰乙酸乙酯 在 硫酸 、 sodium ethanolate 作用下， 生成 bicyclo[7.3.1]tridec-12-en-11-one
  参考文献：
  名称：

  通往1,3-环辛酸酯戊烯的便捷路线

  摘要：

  已经通过外消旋形式通过涉及适当构建的双环[4.2.0]八碳三烯前体的最终旋转开环的途径，以外消旋形式制备了三个以亚甲基桥连的亚甲基桥连的环辛酸酯。

  DOI：

  10.1016/0040-4039(88)80011-x

文献信息

• Structural analysis of cis-[n.3.1]bicyclic ketones by x-ray crystallography. Impact of the observed conformational crossover by .pi.-facially diastereoselective nucleophilic additions to this class of ketones and on the stereochemical course of electrophilic reactions involving their methylene analogs
  作者：Leo A. Paquette、Ted L. Underiner、Judith C. Gallucci

  DOI：10.1021/jo00027a018

  日期：1992.1

  X-ray crystallographic studies clearly show that cis-[n.3.1]bicyclic ketones 1 having n equal to 7 or less are conformationally predisposed such that the rigid chair cyclohexanone ring projects the polymethylene chain diaxially. In contrast, an increase in belt size to n = 9 is adequate to allow adoption of diequatorial geometry without evidence for dynamic chair-chair interconversion. These divergent ground-state characteristics are believed to persist in the methylene derivatives 2. In order to evaluate the impact of this stereochemical crossover on the facial stereoselectivity of nucleophilic attack on 1 and electrophilic capture by 2, the following reactions were examined: hydride and dissolving metal reduction, organometallic additions, condensation with dimethyloxosulfonium methylide, epoxidation, osmylation, oxymercuration, and cycloadditions involving chlorosulfonyl isocyanate and dichloroketene. The presence of an axially oriented loop strongly curtails otherwise favored axial approach by these reagents. With these systems, a strong preference for less hindered equatorial approach is observed. Although the (CH2)9 series is subject to near-identical inductive contributions from the polymethylene belt, the overwhelming diequatorial bias of this belt does not introduce a comparable steric bias and a general (although not exclusive) preference for axial attack is noted. These substitution effects are compared to those of the 4-tert-butylcyclohexyl analogues.
• Is pseudorotation the operational pathway for bond shifting within [8]annulenes? Probe of planarization requirements by 1,3-annulation of the cyclooctatetraene ring. Kinetic analysis of racemization and 2-D NMR quantitation of .pi.-bond alternation and ring inversion as a function of polymethylene chain length
  作者：Leo A. Paquette、Ting Zhong Wang、Jihmei Luo、Charles E. Cottrell、Amy E. Clough、Larry B. Anderson

  DOI：10.1021/ja00157a038

  日期：1990.1
• Synthetic Studies Involving Bridgehead α,β-Unsaturated Ketones: Protocols for Regiocontrolled α-Methylation
  作者：Leo A. Paquette、Hui-Ling Wang、Zhuang Su

  DOI：10.1055/s-1998-2127

  日期：1998.8
• WANG, TING-ZHONG;PAQUETTE, LEO A., TETRAHEDRON LETT., 29,(1988) N 1, 41-44
  作者：WANG, TING-ZHONG、PAQUETTE, LEO A.

  DOI：——

  日期：——
• YAMAGA HIROSHI; FUJISE YUTAKA; ITO SHO, TETRAHEDRON LETT., 28,(1987) N 5, 585-588
  作者：YAMAGA HIROSHI、 FUJISE YUTAKA、 ITO SHO

  DOI：——

  日期：——