exo-3-methyl-endo-tricyclo<5.2.1.0^2,6>deca-4,8-dien-endo-3-ol | 52916-88-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: exo-3-methyl-endo-tricyclo<5.2.1.0^2,6>deca-4,8-dien-endo-3-ol
• 英文别名: (+/-)-1-methyl-(3ac,7ac)-3a,4,7,7a-tetrahydro-4r,7c-methano-inden-1t-ol；(1R,2S,3R,6R,7S)-3-methyltricyclo[5.2.1.02,6]deca-4,8-dien-3-ol
• CAS: 52916-88-8；100058-39-7；123930-75-6
• 化学式: C₁₁H₁₄O
• 分子量: 162.232
• InChiKey: ZMFYEROFOQQEEC-NZHYYXIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  exo-3-methyl-endo-tricyclo<5.2.1.0^2,6>deca-4,8-dien-endo-3-ol 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 以90%的产率得到exo-9-bromo-6-methyl-7-oxatetracyclo<6.3.0.0^2,6.0^3,10>undec-4-ene
  参考文献：
  名称：

  Regio- and stereoselectivity of additions of organometallics to - and -tricyclo[5.2.1.02,6]deca-4,8-dien-3-ones

  摘要：

  The regio- and stereoselectivity of the addition of selected organometallics to endo- and exo-tricyclodecadienones 12, 18 and 21 are described. RLi and R(2)Culi add with complete 1,2- and 1,4-regioselectivity, respectively, the additions of RMgX and RMgX/CuX are only slightly less selective. Additions to 12 and 21 occur from the convex exo-face only, irrespective of the nature of both reagent and substrate. In contrast, organometallic species add from both the concave and the convex face to tricyclic ester 18, with a selectivity that depends on the type of organometallic reagent. The observed stereoselectivities of the additions are rationalized by invoking steric control by the C-8-C-9 ethylene bridge in 12, by the C-10 methylene bridge in 21 and by both the C-8-C-9 ethylene bridge and the exo-ester function at C-2 in tricyclic ester 18.

  DOI：

  10.1016/s0040-4020(01)81817-2
• 作为产物：
  描述：

  exo-4,5-epoxy-endo-tricyclo[5.2.1.0^2,6]dec-8-en-3-one 在 一水合肼 、 溶剂黄146 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 12.75h， 生成 exo-3-methyl-endo-tricyclo<5.2.1.0^2,6>deca-4,8-dien-endo-3-ol
  参考文献：
  名称：

  从双环戊二烯到α-cuparenone的对映体收敛路线

  摘要：

  通过采用脂肪酶催化的动力学水解方法，已设计出由双环戊二烯向α-cuparenone转化的正式对映体路线。

  DOI：

  10.1039/c39890000271

文献信息

• TEMPO/NaIO₄−SiO₂: A Catalytic Oxidative Rearrangement of Tertiary Allylic Alcohols to β-Substituted α,β-Unsaturated Ketones
  作者：Masatoshi Shibuya、Masaki Tomizawa、Yoshiharu Iwabuchi

  DOI：10.1021/ol801673r

  日期：2008.11.6

  The novel catalytic method for the oxidative rearrangement of tertiary allylic alcohols to beta-substituted alpha,beta-unsaturated ketones is described. TEMPO/NaIO4-SiO2 causes facile and efficient oxidative rearrangement of various acyclic substrates as well as medium-sized and macrocyclic substrates.

  描述了一种新的催化方法，用于将叔烯丙基醇氧化重排为β-取代的α，β-不饱和酮。TEMPO / NaIO4-SiO2导致各种无环底物以及中型和大环底物的便捷有效氧化重排。
• Preparation and Thermal Rearrangement of Several Dicyclopentadiene Derivatives
  作者：Myron Rosenblum

  DOI：10.1021/ja01569a050

  日期：1957.6
• Pentacyclodecane chemistry. X. Synthesis and acetolysis of syn- and anti-6-methylpentacyclo[5.3.0.02,503,9.04,8]dec-6-yl p-toluenesulfonate. Further evidence concerning bridging in secondary 1,3-bishomocubyl systems
  作者：Wendell L. Dilling、John A. Alford

  DOI：10.1021/ja00818a040

  日期：1974.5
• TAKANO, SEIICHI;INOMATA, KOHEI;OGASAWARA, KUNIO, J. CHEM. SOC. CHEM. COMMUN.,(1989) N, C. 271-272
  作者：TAKANO, SEIICHI、INOMATA, KOHEI、OGASAWARA, KUNIO

  DOI：——

  日期：——