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(2R,3S)-1,2-cyclohexylidenetridecane-1,2,3-triol | 654077-32-4

中文名称
——
中文别名
——
英文名称
(2R,3S)-1,2-cyclohexylidenetridecane-1,2,3-triol
英文别名
(2R,3S)-1,2-cyclohexylidenedioxytridecan-3-ol;(2R,3S)-1,2-O-cyclohexylidenetridecane-3-ol;1-[(2R)-1,4-dioxaspiro[4.5]dec-2-yl]undecan-1-ol;(1S)-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]undecan-1-ol
(2R,3S)-1,2-cyclohexylidenetridecane-1,2,3-triol化学式
CAS
654077-32-4
化学式
C19H36O3
mdl
——
分子量
312.493
InChiKey
IVFHSYBCSBSMHB-ZWKOTPCHSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    5.9
  • 重原子数:
    22
  • 可旋转键数:
    10
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    1.0
  • 拓扑面积:
    38.7
  • 氢给体数:
    1
  • 氢受体数:
    3

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

点击查看最新优质反应信息

文献信息

  • Metal-Dependent Reaction Tuning with Cyclopentylmetal Reagents: Application to the Asymmetric Synthesis of (+)-α-Conhydrine and (<i>S</i>)-2-Cyclopentyl-2-phenylglycolic Acid
    作者:Siddharth Roy、Anubha Sharma、Soumyaditya Mula、Subrata Chattopadhyay
    DOI:10.1002/chem.200801603
    日期:2009.2.2
    The reaction of halocyclopentane organometallic reagents can be tuned by the choice of metal (see scheme). Cyclopentylmagnesium bromide reduces aldehydes and ketones to the corresponding alcohols. However, in the presence of ZnCl2, normal Grignard addition to the ketones gives tertiary alcohols with complete diastereoselectivity. These protocols were used in the asymmetric synthesis of two medicinally
    调整:卤环戊烷有机金属试剂的反应可通过选择金属来调整(参见方案)。环戊基溴化镁将醛和酮还原为相应的醇。然而,在存在ZnCl 2的情况下,向酮中常规的格利雅(Grignard)加成会产生具有完全非对映选择性的叔醇。这些规程用于两种医学上重要的化合物的不对称合成。
  • Diastereoselective Synthesis of<i>syn</i>-Alkanetriols from a Glyceral Derivative via<scp>k</scp>-Selectride Reduction: Application to the Synthesis of a Pheromone of the Sugarcane Weevils
    作者:Angshuman Chattopadhyay、Bhaskar Dhotare、Avinash Salaskar
    DOI:10.1055/s-2003-42422
    日期:——
    k-selectride reduction of commercially available d-mannitol­ derived ketones 2b-i produced the corresponding alcohols 3b-i in good yields and with absolute syn-selectivity in almost all the cases. It was proposed that the bulky cyclohexylidene moiety of 3 has a significant role in favoring the reduction with k-selectride via Felkin-Anh model. Subsequently, one of the reduction product 3c has been exploited to synthesize the pheromone I of sugarcane weevil.
    使用商业可得的d-甘露醇衍生酮类(2b-i)进行k-selectride还原反应,得到了相应的醇类(3b-i),产率良好且在几乎所有情况下均表现出绝对的顺式选择性。提出3中的体积较大的环己烯基部分在促进与k-selectride的还原反应中起到了重要作用,符合Felkin-Anh模型。随后,其中一个还原产物3c被用来合成甘蔗象甲虫的信息素I。
  • A chemoenzymatic asymmetric synthesis of the hydroxy acid segment of schulzeines B and C
    作者:Sucheta Biswas、Subrata Chattopadhyay、Anubha Sharma
    DOI:10.1016/j.tetasy.2009.12.020
    日期:2010.1
    an enantioselective lipase-catalyzed acylation of a secondary alcohol, (ii) an efficient diastereoselective addition of an alkyl-lithium reagent to a glyceraldehyde derivative, (iii) conversion of an epoxide to a one-carbon homologated allylic alcohol via a sulphorane addition, and (iv) a cross metathesis between two chiral allylic alcohols and subsequent functionalization to obtain the ethyl ester of
    通过构建模块方法开发了标题化合物的化学酶促不对称合成方法。合成的关键步骤是(i)对映选择性脂肪酶催化的仲醇酰化反应;(ii)烷基锂试剂向甘油醛衍生物的高效非对映选择性加成反应;(iii)环氧化物转化为单-碳通过磺胺加成使烯丙基醇均化,和(iv)两种手性烯丙基醇之间的交叉复分解和随后的官能化,以获得磺胺嘧啶的羟基酸单元的乙酯。
  • An enantiodivergent synthesis of both (+)- and (−)-disparlure from (R)-2,3-cyclohexylideneglyceraldehyde
    作者:Akhil Kumar Dubey、Angshuman Chattopadhyay
    DOI:10.1016/j.tetasy.2011.08.013
    日期:2011.7
    Reduction of ketone 3 derived from (R)-2,3-cyclohexylideneglyceraldehyde 1 with some common hydrides took place with syn-selectivity. The resulting major product 4a has been exploited as a common chiral template to prepare both enantiomers 1a,b of disparlure. (C) 2011 Elsevier Ltd. All rights reserved.
  • (<i>R</i>)-2,3-Cyclohexylideneglyceraldehyde, a Chiral Pool Synthon for the Synthesis of 2-Azido-1,3-diols
    作者:Abdul Rouf、Mushtaq A. Aga、Brijesh Kumar、Subhash C. Taneja
    DOI:10.1002/hlca.201400344
    日期:2015.6
    A new approach was proposed for the synthesis of 2‐azido‐1,3‐diols from easily available and inexpensive chiral pool synthon (R)‐2,3‐O‐cyclohexylidene‐D‐glyceraldehyde, through Mitsunobu azidation of 1,2‐diols. Both C(2) and C(1) azides in variable ratios were obtained in alkyl substituted diols with C(2) as the major one.
    有人提出了一种新的方法,通过Mitsunobu叠合1,2- ,从容易获得且廉价的手性池合成子(R)-2,3- O-环己叉基-D-甘油醛合成2-叠氮基1,3,2-二醇。二醇。在以C(2)为主要成分的烷基取代的二醇中获得了可变比率的C(2)和C(1)叠氮化物。
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