(1R,2R)-1-phenyl-1,2-cyclohexanediol | 4912-59-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R)-1-phenyl-1,2-cyclohexanediol
• 英文别名: (+)-(1R,2R)-1-phenylcyclohexane-cis-1,2-diol；1(R),2(R)-(+)-1-phenylcyclohexane-1,2-diol；(1R,2R)-1-phenyl-1,2-cyclohexane-diol；(1R,2R)-1-phenylcyclohexane-1,2-diol；(R,R)-1-phenyl-1,2-cyclohexanediol；(R,R)-1-phenylcyclohexane-1,2-diol
• CAS: 4912-59-8；17540-15-7；27167-34-6；34281-90-8；52305-68-7；134780-67-9；134780-68-0；135095-89-5；125132-75-4
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: QHNHEYDAIICUDL-VXGBXAGGSA-N

物化性质

• 熔点：
  121-123 °C(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2R)-1-phenyl-1,2-cyclohexanediol 在 lithium aluminium tetrahydride 、 sodium azide 、 高氯酸 、 乙酸酐 、 sodium hydride 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 128.5h， 生成
  参考文献：
  名称：

  Homochiral ligands derived from cis-1-phenylcyclohexane-1,2-diol and cis-2-azido-2-phenylcyclohexanol

  摘要：

  Homochiral ligands (R,R)-2, (R,R)-3a, (R,R)-3b, (S,S)-4a, and (S,S)-4b were prepared from cis-1-phenylcyclohexane-1,2-diol or cis-2-azido-2-phenylcyclohexanol and were tested as ligands for the nucleophilic addition of alkyllithiums to benzaldehyde 4-anisidineimine. While moderate enantioselectivities (up to 43% e.e.) were observed with (R,R)-3b and (S,S)-4a, (R,R)-2 and (R,R)-3a did not show enantioselectivities. Homochiral secondary amines (S,S)-6a and (S,S)-6b were also prepared from cis-2-azido-2-phenylcyclohexanol. Moderate enantioselectivities (up to 50%) were observed-when they were used as chiral lithium amide base precursors for the deprotonation of 4-t-butylcyclohexanone. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00552-1
• 作为产物：
  描述：

  cis-acetic acid 2-hydroxy-2-phenyl-cyclohexyl ester 以 乙醇 、 水 为溶剂， 反应 11.0h， 生成 (1R,2R)-1-phenyl-1,2-cyclohexanediol
  参考文献：
  名称：

  Naemura, Koichiro; Miyabe, Hajime; Shingai, Yasuhiro, Journal of the Chemical Society. Perkin transactions I, 1993, # 9, p. 1073 - 1078

  摘要：

  DOI：

文献信息

• A mechanistically designed mono-cinchona alkaloid is an excellent catalyst for the enantioselective dihydroxylation of olefins
  作者：E.J. Corey、Mark C. Noe、Michael J. Grogan

  DOI：10.1016/s0040-4039(00)78237-2

  日期：1994.8

  advanced regarding the origin of enantioselectivity in the OsO4-promoted dihydroxylation of olefins catalyzed by bis-cinchona alkaloid derivatives such as 1, specifically strong evidence for reaction via transition state assembly 2, the mono-quinidine derivative 3 was selected as a promising catalytic ligand. The experimental observation of high enantioselectivity promoted by 3 provides additional

  根据最近提出的关于OsO 4促进的由双金鸡纳生物碱衍生物（例如1）催化的烯烃的二羟基化中对映选择性的起源的想法，特别是有强有力的证据证明通过过渡态组装体2可以进行反应，单奎尼丁衍生物3是被选为有前途的催化配体。由3促进的高对映选择性的实验观察提供了有利于过渡态2的其他证据。
• Green Organocatalytic Dihydroxylation of Alkenes
  作者：Alexis Theodorou、Ierasia Triandafillidi、Christoforos G. Kokotos

  DOI：10.1002/ejoc.201601144

  日期：2017.3.17

  A cheap, green and metal-free one-pot procedure for the dihydroxylation of alkenes is described. H2O2 was employed as the oxidant and 2,2,2-trifluoroacetophenone as the organocatalyst, leading to a highly sustainable protocol, where a variety of homoallylic alcohols, amino-alkenes and double bonds were converted into the corresponding polyalcohols in high to excellent yields. This manifold takes advantage

  描述了一种用于烯烃二羟基化的廉价、绿色和无金属的一锅法。使用 H2O2 作为氧化剂，使用 2,2,2-三氟苯乙酮作为有机催化剂，形成了一种高度可持续的方案，其中各种高烯丙醇、氨基烯烃和双键以高产率转化为相应的多元醇。该歧管利用环氧化反应，然后对反应混合物进行原位酸处理，水环打开三元环，产生所需的产物。
• Markedly enhanced recyclability of osmium catalyst in asymmetric dihydroxylation reactions by using macroporous resins bearing both residual vinyl groups and quaternary ammonium moieties
  作者：Kwang Jin Kim、Han Young Choi、Soon Ho Hwang、Yil Sung Park、Eun Kyung Kwueon、Doo Seong Choi、Choong Eui Song

  DOI：10.1039/b504223b

  日期：——

  Markedly enhanced recyclability of osmium catalyst in asymmetric dihydroxylation has been achieved by using osmylated macroporous resins bearing both residual vinyl groups and quaternary ammonium moiety.

  通过使用同时含有残留乙烯基团和季铵基团的锇配合大孔树脂，显著提高了不对称二羟基化反应中锇催化剂的可回收性。
• Preparation, Characterization and Catalytic Properties of Polyaniline-Supported Metal Complexes
  作者：Boyapati M. Choudary、Moumita Roy、Sarabindu Roy、M. Lakshmi Kantam、Bojja Sreedhar、Karasala Vijay Kumar

  DOI：10.1002/adsc.200606077

  日期：2006.8

  Polyaniline-supported Sc, In, Pd, Os and Re catalysts were prepared by using a simple protocol and the thus prepared catalysts were well characterized using FTIR, XPS, UV-Vis/DRS, TGA-DTA. All the catalysts were successfully employed in a wide range of organic transformations such as cyanation and allylation of carbonyl compound, Suzuki coupling of aryl halides and boronic acids, and, most importantly

  聚苯胺负载的Sc，In，Pd，Os和Re催化剂采用简单的操作流程制备，并使用FTIR，XPS，UV-Vis / DRS，TGA-DTA对如此制备的催化剂进行了很好的表征。所有催化剂均成功用于各种有机转化中，例如羰基化合物的氰化和烯丙基化，芳基卤化物和硼酸的Suzuki偶联，以及最重要的是，用于烯烃的不对称二羟基化以提供旋光的邻位二醇。通过简单的过滤将所有催化剂从反应混合物中分离出来，并以一致的活性重复使用五个循环，而没有明显的金属从载体中浸出。
• A New Practical Method for the Osmium-Catalyzed Dihydroxylation of Olefins­ using Bleach as the Terminal Oxidant
  作者：Matthias Beller、Gerald M. Mehltretter、Santosh Bhor、Markus Klawonn、Christian Döbler、Uta Sundermeier、Markus Eckert、Hans-Christian Militzer

  DOI：10.1055/s-2003-36826

  日期：——

  A general procedure for the osmium-catalyzed dihydroxylation of various olefins using bleach as oxidant is reported for the first time. Aromatic and aliphatic olefins yield the corresponding cis-1,2-diols in the presence of dihydroquinine or dihydroquinidine derivatives (Sharpless ligands) with good to excellent chemo- and enantioselectivities under optimized pH conditions. In the presence of a small

  首次报道了使用漂白剂作为氧化剂对各种烯烃进行锇催化二羟基化的一般程序。芳香族和脂肪族烯烃在二氢奎宁或二氢奎尼丁衍生物（Sharpless 配体）存在下产生相应的 cis-1,2-二醇，在优化的 pH 条件下具有良好至优异的化学和对映选择性。在少量过量的漂白剂作为再氧化剂的情况下，即使在 0°C 也会发生快速二羟基化。在最佳反应条件下，可以将末端脂肪族和芳香族烯烃以及内烯烃二羟基化。氧化剂的低价和漂白剂的简单处理使这种二羟基化变体对进一步的应用具有吸引力。