trans-(2-Phenylcyclohexyl)methanol | 36359-51-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trans-(2-Phenylcyclohexyl)methanol
• 英文别名: (+/-)-trans-2-phenylcyclohexanemethanol；[(1R,2R)-2-Phenylcyclohexyl]methanol
• CAS: 36359-51-0
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: MJXMWXWVIXLIGK-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  trans-(2-Phenylcyclohexyl)methanol 、 1,1'-(phenyl-λ³-iodanediyl)bis(4-(trifluoromethyl)pyridinium)trifluoromethanesulfonate 以46%的产率得到trans-(6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-2-yl)(phenyl)iodonium triflate
  参考文献：
  名称：

  芳烃 C-H 醚化的 Umpolung 策略导致由 I(III) N-连接的高价碘试剂启用的官能化色烷

  摘要：

  通过C-H键和侧醇的分子内脱氢偶联直接形成芳基C-O键代表了强大的合成转化。在此，我们报告了一种通过 I(III) N- HVI 试剂介导的 umpoled 醇环化进行分子内芳烃 C-H 醚化的方法。这种方法通过级联环化-碘盐形成从伯醇、仲醇和叔醇中获得官能化色满支架，后者为下游衍生化提供了通用的功能处理。计算研究支持通过 I(III) 配体交换初始形成 umpoled O-中间体，然后是竞争性直接和螺环化/1,2-转变途径。

  DOI：

  10.1002/adsc.202100809
• 作为产物：
  描述：

  1,4-二苯基-1,3丁二烯 在 sodium tetrahydroborate 、 臭氧 、 magnesium 作用下， 反应 5.08h， 生成 trans-(2-Phenylcyclohexyl)methanol
  参考文献：
  名称：

  Chemistry of substituted (2-butene-1,4-diyl)magnesium: a facile approach to complex carbocycles, functionalized ketones and alcohols, and silicon-containing heterocycles

  摘要：

  Highly reactive magnesium reacts with a wide variety of substituted 1,3-dienes to give the corresponding substituted (2-butene-1,4-diyl)magnesium complexes. Reactions of symmetrical (2-butene-1,4-diyl)magnesium with alpha,omega-alkylene dihalides form three-, four-, five-, and six-membered carbocycles. Significantly, the cyclizations are always stereospecific and completely regioselective. Depending on the initial 1,3-diene and specific electrophiles, uncyclized products can be obtained. Stepwise reactions of (2,3-dimethyl-2-butene-1,4-diyl)magnesium with two different electrophiles afford polyfunctionalized ketones with the generation of a quaternary center. Formal 1,2-additions can be effected in this manner. Substituted five- and six-membered cyclic ketones can also be synthesized in one step by this approach. Treatment of unsymmetrical (2-butene-1,4-diyl)magnesium complexes with triorganosilyl chlorides followed by cyclohexanone results in additions across a terminal double bond with high regioselectivity. Silicon-containing heterocycles or spiro compounds can be readily synthesized by using the bis-Grignard reagents.

  DOI：

  10.1021/jo00009a034

文献信息

• Alkyl Ethers as Traceless Hydride Donors in Brønsted Acid Catalyzed Intramolecular Hydrogen Atom Transfer
  作者：Dhika Aditya Gandamana、Bin Wang、Ciputra Tejo、Benoit Bolte、Fabien Gagosz、Shunsuke Chiba

  DOI：10.1002/anie.201801953

  日期：2018.5.22

  A new protocol for the deoxygenation of alcohols and the hydrogenation of alkenes under Brønsted acid catalysis has been developed. The method is based on the use of either a benzyl or isopropyl ether as a traceless hydrogen‐atom donor, and involves an intramolecular hydride transfer as a key step, which is achieved in a regio‐ and stereoselective manner.

  已经开发了在布朗斯台德酸催化下醇的脱氧和烯烃的氢化的新方案。该方法基于使用苄基或异丙基醚作为无痕氢原子供体，并且涉及分子内氢化物转移作为关键步骤，这是通过区域和立体选择性方式实现的。
• Auxiliary-directed peroxidation of 1,4-dienes
  作者：Patrick H. Dussault、Todd A. Anderson、Michael R. Hayden、Kevin J. Koeller、Q. Jason Niu

  DOI：10.1016/0040-4020(96)00744-2

  日期：1996.9

  diastereoselection is also observed for distal addition of 3O2. The extent of olefin isomerization observed during radical oxygenations can be correlated with steric constraints on the intermediate pentadienyl and peroxyl radicals and may be relevant to literature reports of olefin isomerization during enzymatic oxygenations of unnatural fatty acids.

  将单线态氧（1 O 2）添加到辅助束缚的1,4-二烯的近端烯烃中以及将三线态氧（3 O 2）添加到相应的戊二烯基的近端位置中均产生适度的共轭二烯氢过氧化物到高的非对映异构体过量。由于缺乏对烯烃构象的控制，对于向Z，Z-庚二烯的远端烯烃加成1 O 2，观察到可忽略的立体选择。尽管有证据表明戊二烯基是高度受约束的中间体，但远端添加3 O 2的非对映选择性也很差。。自由基氧合期间观察到的烯烃异构化程度可能与中间戊二烯基和过氧自由基的空间限制相关，并且可能与非天然脂肪酸酶促氧合期间烯烃异构化的文献报道有关。
• Chiral alcohol-induced diastereoselective conjugate addition and cyclization
  作者：Chenglin Fang、Hiroshi Suemune、Kiyoshi Sakai

  DOI：10.1016/s0040-4039(00)97723-2

  日期：1990.1

  Conjugate addition of organocuprate reagents to α,β-unsaturated esters of chiral trans-cyclohexanediol proceeded diastereoselectively, and the intramolecular trapping of the generated enolate also afforded asymmetric cyclization products.

  向手性反式-环己二醇的α，β-不饱和酯中共轭添加有机铜试剂，非对映选择性地进行，分子内捕获所产生的烯醇化物也提供了不对称的环化产物。
• Organolanthanide-Catalyzed Cyclization/Boration of 1,5- and 1,6-Dienes
  作者：Gary A. Molander、Dirk Pfeiffer

  DOI：10.1021/ol006841s

  日期：2001.2.1

  [figure: see text] 1,5- and 1,6-Dienes undergo a cyclization/boration reaction in the presence of a catalytic amount of Cp*2Sm.THF. The resulting organoboranes can be oxidized to the corresponding primary cyclic alcohols using standard conditions.

  [图：见正文]在催化量的Cp * 2Sm.THF存在下，1,5-和1,6-二烯进行环化/硼化反应。可以使用标准条件将所得的有机硼烷氧化为相应的伯环醇。
• Langlois; Rapin; Meingan, European Journal of Medicinal Chemistry, 1976, vol. 11, # 6, p. 493 - 499
  作者：Langlois、Rapin、Meingan、et al.

  DOI：——

  日期：——