endo-9-Oxatetracyclo<5.3.1.0^2.6.0^8.10>undec-3-ene | 4387-46-6

• 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: endo-9-Oxatetracyclo<5.3.1.0^2.6.0^8.10>undec-3-ene
• 英文别名: endo-9-Oxatetracyclo[5.3.1.0^2.6.0^8.10]undec-3-ene；(1S,2R,6S,7R,8R,10S)-9-oxatetracyclo[5.3.1.02,6.08,10]undec-3-ene
• CAS: 4387-46-6；52154-84-4；52882-08-3
• 化学式: C₁₀H₁₂O
• 分子量: 148.205
• InChiKey: HHCQUXXWMVYOTM-TUUAOYNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  endo-9-Oxatetracyclo<5.3.1.0^2.6.0^8.10>undec-3-ene 在 lithium diethylamide 、 pyridinium chlorochromate 作用下， 生成 (+/-)-(3ac,7ac)-1,3a,4,6,7,7a-hexahydro-4r,7c-methano-inden-5-one 、 (1S,2S,6R,7S)-tricyclo[5.2.1.02,6]dec-3-en-8-one
  参考文献：
  名称：

  固定在刚性分子中的环戊烯酮和苯乙烯的分子内光反应

  摘要：

  制备了8-和9-苯基三环[5.2.1.0 2,6 ] deca-4,8-​​dien-3-one，并研究了它们的光化学行为。尽管每种化合物在直接照射下均给出分子内[2 + 2]环加成产物，但是发现，根据苯乙烯和烯酮部分的取向，各个反应路径的细节彼此显着不同。

  DOI：

  10.1016/0040-4039(95)01311-5
• 作为产物：
  描述：

  3,8-dioxapentacyclo<6.3.1.0^2,4.0^6,11.0^7,9>dodecane 在 三苯基膦 作用下， 反应 6.0h， 以8%的产率得到endo-9-Oxatetracyclo<5.3.1.0^2.6.0^8.10>undec-3-ene
  参考文献：
  名称：

  Kas'yan, L. I.; Stepanova, N. V.; Galafeeva, M. F., Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, p. 109 - 112

  摘要：

  DOI：

文献信息

• Substrate-Induced Diastereoselectivity in the Dimethyldioxirane Epoxidation of Simple Alkenes and Dienes
  作者：Amalia Asouti、Lazaros P. Hadjiarapoglou

  DOI：10.1055/s-2001-18751

  日期：——

  Various alkenes and dienes, such as (R)- or (S)-limonene 2, 2-carene 6, 3-carene 8, (R)-α-pinene 10, (S)-α-pinene 12, and endo-dicyclopentadiene 14 were transformed into the corresponding mono- and bis-epoxides by epoxidation with dimethyldioxirane (as an acetone solution). The selectivity observed in these epoxidations is explained by the assumption of hydrogen bonding between bridge protons and the dioxirane.

  各种烯烃和二烯烃，例如（R）-或（S）-柠檬烯2、2-蒈烯6、3-蒈烯8、（R）-α-蒎烯10、（S）-α-蒎烯12以及endo-二环戊二烯14，通过二甲基二氧杂环丙烷（以丙酮溶液形式）的环氧化反应，被转化为相应的单环氧和双环氧化合物。在这些环氧化过程中观察到的选择性可以通过桥连质子与二氧杂环丙烷之间氢键的假设来解释。
• Regioselective and diastereoselective dimethyldioxirane epoxidation of substituted norbornenes and hexamethyl Dewar benzene
  作者：Amalia Asouti、Lazaros P Hadjiarapoglou

  DOI：10.1016/s0040-4039(99)02113-9

  日期：2000.1

  endo-dicyclopentadiene 1, exo-dicyclopentadiene 5, 5-methylenebicyclo[2.2.1]hept-2-ene 8 and hexamethyl Dewar benzene 10 were transformed into the corresponding mono- and bis-epoxides by epoxidation with dimethyldioxirane (as an acetone solution).

  各种取代的降冰片烯，如内切-dicyclopentadiene 1，外切-dicyclopentadiene 5，5-亚甲基[2.2.1]庚-2-烯8和六甲基杜瓦苯10，通过用二甲基二环氧化转化成相应的单-和双-环氧化物（作为丙酮溶液）。
• Oxidation of organic substrates by a molecular oxygen/aldehyde/heteropolyoxometalate system
  作者：Masatoshi Hamamoto、Kouichi Nakayama、Yutaka Nishiyama、Yasutaka Ishii

  DOI：10.1021/jo00075a043

  日期：1993.11

  Heteropolyoxometalate-catalyzed oxidations of organic compounds such as olefins and cyclic ketones with molecular oxygen in the presence of an aldehyde were examined. Olefins were epoxidized with dioxygen in the presence of 2 equiv of 2-methylpropanal under the influence of a catalytic amount of the mixed heteropolyoxometalate NPV6Mo6 (3) to give the corresponding epoxides in moderate to good yields. This catalytic oxidation method was also applied to the epoxidation of allylic and homoallylic alcohols. In the absence of olefins, the aldehydes were efficiently converted into the corresponding carboxylic acids. In addition, the Baeyer-Villiger oxidation of cyclic ketones was accomplished by using benzaldehyde instead of 2-methylpropanal as the aldehyde.
• Oxidation of olefins and alcohols by peroxo-molybdenum complex derived from tris(cetylpyridinium) 12-molybdophosphate and hydrogen peroxide
  作者：Yasutaka Ishii、Kazumasa Yamawaki、Tsutomu Yoshida、Toshikazu Ura、Masaya Ogawa

  DOI：10.1021/jo00385a042

  日期：1987.5
• Schnurpfeil, D., Journal fur praktische Chemie (Leipzig 1954), 1983, vol. 325, # 5, p. 842 - 847
  作者：Schnurpfeil, D.

  DOI：——

  日期：——