(1R,3R)-cyclohexane-1,2,3-triol | 62445-01-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,3R)-cyclohexane-1,2,3-triol
• 英文别名: cyclohexane-1,2,3-triol；(1R)-cyclohexane-1r,2,3t-triol；(1R)-Cyclohexan-1r,2,3t-triol；(1R)-Cyclohexantriol-(1r.2.3t)；(1R:3R)-Cyclohexantriol-(1.2.3)；(-)-L-1,2/3-Cyclohexantriol
• CAS: 62445-01-6
• 化学式: C₆H₁₂O₃
• 分子量: 132.159
• InChiKey: IZSANPWSFUSNMY-RFZPGFLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,3R)-cyclohexane-1,2,3-triol 在 palladium on activated charcoal 四氮唑 、 氢气 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 (+/-)-(1α,2α,3β)-cyclohexane-triol-tris(phosphate)
  参考文献：
  名称：

  Synthesis of α-trinositol related analogues. Structure-activity (analgesic and anti-inflammatory) relationships

  摘要：

  alpha-Trinositol analogues, including methyl ethers, deoxy, oxa and aza derivatives were prepared. The parent compound possesses weak analgesic and anti-inflammatory properties. Removal of the non-phosphorylated hydroxyls generates a compound devoid of analgesic activity but which retains the anti-inflammatory property of the parent compound. The protection of these hydroxyls as methyl ethers leads to compounds which keep their anti-inflammatory activity, whereas the replacement of the cyclohexane carbone backbone by a tetrahydropyrane or a piperidine ring leads to compounds which increase the pain.

  DOI：

  10.1016/s0223-5234(97)84017-2
• 作为产物：
  描述：

  (+/-)-2,2-dimethyl-(3ar,7ac)-hexahydro-benzo[1,3]dioxol-4c-ol 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.0h， 生成 (1R,3R)-cyclohexane-1,2,3-triol
  参考文献：
  名称：

  酶法合成1,2,3-环己三醇的手性异亚丙基衍生物

  摘要：

  2,3-O-异亚丙基-1-环己醇手性结构单元的制备是通过酶解其外消旋的乙酸酯或丁酸正丁酯而获得的高对映体纯度。

  DOI：

  10.1016/s0040-4039(00)99201-3

文献信息

• Molybdenum-Catalyzed Hydroxyl-Directed <i>Anti</i>-Dihydroxylation of Allylic and Homoallylic Alcohols
  作者：Pei Fan、Shixia Su、Chuan Wang

  DOI：10.1021/acscatal.8b01449

  日期：2018.8.3

  A catalytic hydroxyl-directed anti-dihydroxylation of allylic and homoallylic alcohols has been developed. This operationally simple method was successfully applied to the direct anti-monodihydroxylation of allylic alcohols containing at least one distal olefinic unit. Under the catalysis of commercially available MoO2(acac)2, an array of hydroxylated dienes were successfully converted into various

  已经开发了烯丙基和均烯丙基醇的催化羟基定向的抗二羟基化。这种操作简单的方法已成功地应用于含有至少一个远端烯烃单元的烯丙基醇的直接抗单二羟基化反应。在市售MoO 2（acac）2的催化下，使用过氧化氢作为环境良性氧化剂，在有氧条件下，特别是在完全区域选择性和氢键作用下，成功地将一系列羟基化的二烯成功转化为各种1,2,3-三醇。大多数情况下采用非对映特异性途径。
• High Thermal Conductivity Silicon Nitride Ceramic
  作者：Kiyoshi Hirao、Koji Watari、Hiroyuki Hayashi、Mikito Kitayama

  DOI：10.1557/mrs2001.115

  日期：2001.6

  Since the confirmation that nonmetallic single crystals with a diamond-like structure, such as SiC, BP, and AlN, have high intrinsic thermal conductivities of over 300 W m⁻¹ K⁻¹,^1,2 a great deal of effort has been focused on the development of nonoxide polycrystalline ceramics with high thermal conductivity.

  自从确认非金属单晶体（如SiC、BP和AlN）具有高于300 W m⁻¹ K⁻¹的高固有热导率后，人们已经将大量精力集中在开发具有高热导率的非氧化物多晶陶瓷上。
• Molybdenum-Catalyzed Diastereoselective <i>anti</i>-Dihydroxylation of Secondary Allylic Alcohols
  作者：Shixia Su、Chuan Wang

  DOI：10.1021/acs.orglett.9b00735

  日期：2019.4.5

  In this protocol, we report a Mo-catalyzed anti-dihydroxylation of secondary allylic alcohols, providing a general method for the preparation of 1,2,3-triols bearing up to three continuous stereocenters with excellent diastereocontrol. The mechanistic studies reveal that this dihydroxylation reaction consists of two steps and up to excellent diastereomeric ratios of the final triol products can be

  在该协议中，我们报告了钼催化的仲烯丙基醇的抗二羟基化作用，为制备具有多达三个连续立体中心的1,2,3-三醇提供了出色的非对映异构控制的一般方法。机理研究表明，该二羟基化反应包括两个步骤，并且由于初始环氧化中的非对映控制和随后的原位水解中的区域控制都很高，因此最终三醇产物的非对映异构体比例可以达到极高的水平。
• One-Pot Synthesis of 1,2,3-Triols from Allylic Hydroperoxides and a Catalytic Amount of OsO4 in Aqueous Acetone
  作者：Mehmet Gültekin、Cemalettin Alp、Ufuk Atmaca、Murat Çelik

  DOI：10.1055/s-0029-1217965

  日期：2009.10

  Allylic hydroperoxides were converted into the corresponding triols in the presence of a catalytic amount of OsO4. The present reaction involves regeneration of active osmium species by the hydroperoxide functionality and occurs in a diastereoselective manner to form triols in high yields. A plausible mechanism for the formation of 1,2,3-triols from allylic hydroperoxide is presented.

  在催化量的OsO4存在下，烯丙基氢过氧化物被转化为相应的三醇。当前反应涉及通过氢过氧化物功能团再生活性锇物种，并且以立体选择性方式进行，形成高产量的三醇。提出了从烯丙基氢过氧化物生成1,2,3-三醇的合理机理。
• Conversion of racemic allylic hydroperoxides into corresponding chiral 1/2,3-triols by using catalytic OsO$_{4}$ and chiral cinchona ligands in the absence of co-oxidant
  作者：Haydar GÖKSU、Mehmet Serdar GÜLTEKİN

  DOI：10.3906/kim-1411-68

  日期：——

  For the first time, removal of oxygen atoms from allylic hydroperoxide functionality and reintroduction to the double bond was achieved using catalytic OsO$_4}$ and chiral cinchona alkaloid derivatives in an acetone-water mixture to give corresponding chiral 1/2,3-triol with an enantioselectivity up to 99% ee. The hydroperoxide group was used as both a co-oxidant and a source of hydroxyl groups. This protocol is thought to have potential to provide opportunities for chiral synthesis of 1/2,3-triols from corresponding allylic hydroperoxides in the absence of co-oxidant in one stage for the first time in the literature.

  首次利用催化剂OsO$_4}$和手性金鸡纳生物碱衍生物在丙酮-水混合物中实现了烯丙基过氧化氢官能团中的氧原子移除并重新引入双键，合成了对应的手性1/2,3-三醇，其对映选择性高达99% ee。过氧化氢基团既作为协同氧化剂，又作为羟基来源。这一方法被认为有望为从相应的烯丙基过氧化氢在无需协同氧化剂的情况下首度以一步法合成手性1/2,3-三醇提供可能。