(S)-(+)-2-methyl-1-phenyl-2-propen-1-ol | 4383-08-8

• 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: (S)-(+)-2-methyl-1-phenyl-2-propen-1-ol
• 英文别名: (R)-2-methyl-1-phenylprop-2-en-1-ol；(S)-2-methyl-1-phenyl-2-propen-1-ol；isopropylphenylmethanol；(1R)-2-methyl-1-phenylprop-2-en-1-ol
• CAS: 4383-08-8；103729-80-2；147127-68-2；116297-42-8
• 化学式: C₁₀H₁₂O
• 分子量: 148.205
• InChiKey: ZGYBYYJGIKPBFD-SNVBAGLBSA-N

物化性质

• 沸点：
  240℃
• 密度：
  0.998
• 闪点：
  105℃

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2906299090

反应信息

• 作为反应物：
  描述：

  (S)-(+)-2-methyl-1-phenyl-2-propen-1-ol 在 磷化氢 、 sodium hypochlorite 、 碘 、 溶剂黄146 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 6.0h， 生成 (R)-5-(7-(5-benzyl-5-methyl-4,5-dihydroisoxazol-3-yl)-3-(4-fluorophenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)pentanoic acid
  参考文献：
  名称：

  [EN] QUINAZOLINONE-TYPE COMPOUNDS AS CRTH2 ANTAGONISTS
  [FR] COMPOSÉS DE TYPE QUINAZOLINONE CONVENANT COMME ANTAGONISTES DE CRTH2

  摘要：

  该应用程序提供了Formula I的化合物或其药用可接受盐，其中个别变量在此定义，以及制备这些化合物的过程，包括相同的药物组成和它们在治疗与CRTH2受体相关的疾病状态中的用途。

  公开号：

  WO2012051036A1
• 作为产物：
  描述：

  [(2S,3S)-2-甲基-3-苯基-环氧乙烷-2-基]甲醇 在 4-二甲氨基吡啶 、 sodium hydroxide 、 碲化氢 、 sodium formaldehyde sulfoxylate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 (S)-(+)-2-methyl-1-phenyl-2-propen-1-ol
  参考文献：
  名称：

  A tellurium transposition route to allylic alcohols: overcoming some limitations of the Sharpless-Katsuki asymmetric epoxidation

  摘要：

  Good yields of enantiomeric allylic alcohols can be obtained in high enantiomeric excess (ee) by combining the Sharpless-Katsuki asymmetric epoxidation process (SAE) with tellurium chemistry. The advantages of the tellurium process are as follows: (1) the 50% yield limitation on the allylic alcohol in the Sharpless kinetic resolution (SKR) can be overcome; (2) allylic tertiary alcohols which are unsatisfactory substrates in the SKR can be obtained in high optical purity; (3) optically active secondary allylic alcohols with tertiary alkyl substituents (e.g. tert-butyl) at C-1 can be obtained in high ee; (4) optically active sterically congested cis secondary alcohols can be obtained in high ee; and (5) the nuisance of the slow SAE of some vinyl carbinols can be avoided. The key step in the reaction sequence is either a stereospecific 1,3-trans position of double bond and alcohol functionalities or an inversion of the alcohol configuration with concomitant deoxygenation of the epoxide function in epoxy alcohols. Trans secondary allylic alcohols can be converted to cis secondary allylic alcohols by way of erythro epoxy alcohols (glycidols); threo glycidyl derivatives are converted to trans secondary allylic alcohols. These transformations are accomplished by the action of telluride ion, generated in situ from the element, on a glycidyl sulfonate ester. Reduction of elemental Te is conveniently done with rongalite (HOCH2SO2Na) in an aqueous medium. This method is satisfactory when Te2- is required to attack a primary carbon site of a glycidyl sulfonate. In cases where Te2- is required to attack a secondary carbon site, reduction of the tellurium must be done with NaBH4 or LiEt3BH. Elemental tellurium is precipitated during the course of the reactions and can be recovered and reused.

  DOI：

  10.1021/jo00055a029

文献信息

• Synthesis of the C1-C14 Fragment of Sarcoglaucol-16-one via Z-Selective Ando-Type Horner-Wadsworth-Emmons Olefination
  作者：Sabine Laschat、Christoph Gastl

  DOI：10.1055/s-0029-1218825

  日期：2010.8

  A synthetic strategy involving a Z-selective Horner-Wadsworth-Emmons olefination was developed for the preparation of the sarcoglaucolone precursor methyl (2Z,6E)-8-(methoxymeth­oxy)-6-methyl-2-[(3E)-4-methyl-5-oxopent-3-enyl]-9-[(trimethylsilyl)methyl]deca-2,6,9-trienoate. The target compound was isolated in a E/Z ratio of 17:83

  开发了一种涉及Z选择性Horner-Wadsworth-Emmons烯烃化的合成策略，用于制备sarcoglaucolone前体——甲基(2Z,6E)-8-(甲氧基甲氧基)-6-甲基-2-[(3E)-4-甲基-5-氧戊-3-烯基]-9-[(三甲基硅基)甲基]癸-2,6,9-三烯酸酯。目标化合物以E/Z比率17:83被分离。
• Enantioselective Synthesis of Allylic Alcohols via an Oxazaborolidinium Ion Catalyzed Diels−Alder/Retro-Diels−Alder Sequence
  作者：Simon Jones、Damien Valette

  DOI：10.1021/ol902280d

  日期：2009.11.19

  A triflimide-activated oxazaborolidine catalyst successfully promoted the asymmetric Diels−Alder reaction of 9-methylanthracene with methacrolein in high regio- and enantioselectivity. The cycloadduct obtained was subsequently used as a chiral template to access secondary and tertiary allylic alcohols in good to high enantiomeric excess via a cycloreversion by flash vacuum pyrolysis.

  Triflimide活化的恶唑硼烷催化剂在高区域和对映体选择性下，成功地促进了9-甲基蒽与甲基丙烯醛的不对称Diels-Alder反应。随后将获得的环加合物用作手性模板，以通过快速真空热解通过环还原来获得对映体过量至高对映体过量的仲和叔烯丙基醇。
• Novel synthesis of monofluorocyclobutanes by the ring expansion- fluorination of cyclopropylmethanols with an amine-metal fluoride pyridinium poly(hydrogen fluoride)-complex
  作者：Shigekazu Kanemoto、Makoto Shimizu、Hirosuke Yoshioka

  DOI：10.1016/s0040-4039(01)91361-9

  日期：1987.1

  Various new 1-fluoro-1-alkyl(or aryl)-2-substituted cyclobutanes were synthesized stereoselectively from 1-alkyl(or aryl)cyclopropyl carbinols by the ring expansion-fluorination using (iPr)2-KHF2-(HF)n·Py, and 2-hydroxymethyl-1-fluorocyclobutanes were synthesized via a new rearrangement of (1-alkyl(or aryl)cyclopropyl) ethylene oxides.

  使用（i Pr）2 -KHF 2-（HF）通过扩环氟化反应从1-烷基（或芳基）环丙基甲醇立体选择性地合成了各种新的1-氟-1-烷基（或芳基）-2-取代的环丁烷。通过新的（1-烷基（或芳基）环丙基）环氧乙烷重排合成了n ·Py和2-羟甲基-1-氟环丁烷。
• Kinetic Resolution of Aryl Alkenylcarbinols Catalyzed by Fc-PIP
  作者：Bin Hu、Meng Meng、Shanshan Jiang、Weiping Deng

  DOI：10.1002/cjoc.201200410

  日期：2012.6

  An effective kinetic resolution of a variety of aryl alkenylcarbinols catalyzed by nonenzymatic acyl transfer catalyst Fc‐PIP was developed, affording corresponding unreacted alcohols in good to excellent ee value up to 99% and with selectivity factors up to 24.

  开发了有效的动力学拆分非芳基酰基转移催化剂Fc-PIP催化的各种芳基烯基羰基醇的方法，可提供相应的未反应的醇，其ee值高达99％，优良的ee值高达24。
• A highly enantioselective synthesis of chiral allylic alcohols by asymmetric addition of novel mixed reagents of trialkenylbismuthines/dialkylzincs to aldehydes
  作者：Itaru Sato、Noriaki Asakura、Taizo Iwashita

  DOI：10.1016/j.tetasy.2007.10.031

  日期：2007.11

  A novel mixture of reagents of trialkenylbismuthines/dialkylzincs was developed and applied toward the synthesis of chiral allylic alcohols. The chiral β-amino alcohols catalyzed addition of the mixed reagents of trialkenylbismuthines/dialkylzincs to aldehydes gave enantiomerically enriched allylic alcohols with up to 97% ee.

  开发了一种新的三烯基双突变体/二烷基锌试剂混合物，并将其用于手性烯丙基醇的合成。手性β-氨基醇催化将三烯基双突变蛋白/二烷基锌的混合试剂加成到醛中，得到对映体富集的烯丙醇，其ee高达97％。