2-Methyl-4-phenylpent-1-en-3-ol | 220018-40-6

• 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: 2-Methyl-4-phenylpent-1-en-3-ol
• 英文别名: 2-methyl-4-phenylpent-1-en-3-ol
• CAS: 220018-40-6
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: PDIUSCOUFAVFTC-UHFFFAOYSA-N

物化性质

• 沸点：
  261.5±9.0 °C(Predicted)
• 密度：
  0.969±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  2-Methyl-4-phenylpent-1-en-3-ol 在 acetylacetonatodicarbonylrhodium(l) 亚磷酸三苯酯 、 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 20.0~90.0 ℃ 、2.0 MPa 条件下， 反应 48.0h， 生成 (1R*,2R*)-(+/-)-2-Methyl-4-oxo-1-[(1R*)-1-phenylethyl]butyl 2-(diphenylphosphanyl)benzoate
  参考文献：
  名称：

  Substrate-Directed Diastereoselective Hydroformylation: Key Step for the Assembly of Polypropionate Subunits

  摘要：

  Stereoselective hydroformylation of methallylic alcohols of types 3 and 4, that employed the substrate-bound catalyst-directing ortho-diphenyl-phosphanylbenzoyl (o-DPPB) group, was used as a key step for the construction of bifunctionalized stereotriads, which ale central building blocks of polyketide natural products. The required diastereomerically pure syn- and anti- starting methallylic alcohol systems 3 and 4 were obtained either by Cram-selective carbonyl reduction, Frater alkylation, or by chelation-controlled carbonyl reduction. Enantiomerically pure stereotriad building blocks were derived from a combination of an Evans aldol addition and subsequent o-DPPB-directed stereoselective hydroformylation (-->24). A crystal structure analysis for steretriad building block 24 confirmed the relative and absolute configuration of the stereogenic centers. Additionally, it provided evidence for a previously postulated preferred conformation of the catalyst-directing o-DPPB group as well as of the polyketide main chain.

  DOI：

  10.1002/(sici)1521-3765(19991001)5:10<2819::aid-chem2819>3.0.co;2-z
• 作为产物：
  描述：

  2-溴丙烯 、 2-苯基丙醛 在 仲丁基锂 作用下， 以 环己烷 为溶剂， 以80%的产率得到2-Methyl-4-phenylpent-1-en-3-ol
  参考文献：
  名称：

  合成galbonolide B的方法

  摘要：

  已经完成了对加波内酯B 2的C（7）-C（15）片段的方法，其中二烯片段51由（R）-3-叔丁基二甲基甲硅烷基氧戊烷-2-一29通过转化为不饱和酯而组装在图30中，使用该酯对砜47进行酰化，还原性脱硫，使用Wittig反应的亚甲基化和脱保护。根据模型研究，通过醇51的氧化制备的醛62被转化为差向异构醇63的混合物，并使用膦催化的爱尔兰－克莱森重排将其转化为二（亚甲基）十三碳二烯酸65。使用L -（+）-或D可以使酒精67发生尖锐的环氧化-（-）-酒石酸二乙酯具有很高的立体选择性，可得到明显可分辨的环氧化物68和69。使用庚二烯单环氧化物70进行的模型研究导致了单保护的二羟基醛76的合成，因此建立了将加波内酯引入邻位二醇的方案。最后，将醛酸乙酸叔丁酯加到醛78中，然后进行选择性保护，脱保护和环化，完成了大环内酯85的合成。

  DOI：

  10.1039/a805856c

文献信息

• Iron(III) Chloride/Phenylsilane‐Mediated Cascade Reaction of Allyl Alcohols with Maleimides: Synthesis of Poly‐Substituted γ‐Butyrolactones
  作者：Hua Zhang、Xiao‐Yu Zhan、Xu‐Ling Chen、Lei Tang、Shuai He、Zhi‐Chuan Shi、Yu Wang、Ji‐Yu Wang

  DOI：10.1002/adsc.201900843

  日期：2019.11.5

  A iron‐catalyzed free radical cascade reaction of allyl alcohols with N‐substituted maleimides for accessing poly‐substituted γ‐butyrolactones has been developed. In this protocol, various allyl alcohols can open N‐substituted maleimide rings to form allyl ester intermediates, and the allyl ester intermediates can be converted into an allyl ester alkyl radicals and undergo intramolecular free radical

  已开发出铁催化的烯丙醇与N-取代的马来酰亚胺的自由基级联反应，以获取多取代的γ-丁内酯。在该协议中，各种烯丙醇可以打开N-取代的马来酰亚胺环以形成烯丙基酯中间体，并且烯丙基酯中间体可以转化为烯丙基酯烷基，并进行分子内自由基加成环化反应以形成多取代的γ-丁内酯。在该方案中，还可以合成螺-γ-丁内酯化合物。同时，该策略可用于进一步构建完全取代的四氢呋喃。该反应对氧气或湿气不敏感，已以克为单位进行。
• Approaches to a synthesis of galbonolide B
  作者：Peter M. Smith、Eric J. Thomas

  DOI：10.1039/a805856c

  日期：——

  into the unsaturated ester 30, acylation of the sulfone 47 using this ester, reductive desulfurisation, methylenation using a Wittig reaction and deprotection. Following model studies, the aldehyde 62, prepared by oxidation of the alcohol 51, was converted into a mixture of the epimeric alcohols 63 and these were converted into the di(methylene)tridecadienoic acid 65 using a phosphine catalysed Ireland–Claisen

  已经完成了对加波内酯B 2的C（7）-C（15）片段的方法，其中二烯片段51由（R）-3-叔丁基二甲基甲硅烷基氧戊烷-2-一29通过转化为不饱和酯而组装在图30中，使用该酯对砜47进行酰化，还原性脱硫，使用Wittig反应的亚甲基化和脱保护。根据模型研究，通过醇51的氧化制备的醛62被转化为差向异构醇63的混合物，并使用膦催化的爱尔兰－克莱森重排将其转化为二（亚甲基）十三碳二烯酸65。使用L -（+）-或D可以使酒精67发生尖锐的环氧化-（-）-酒石酸二乙酯具有很高的立体选择性，可得到明显可分辨的环氧化物68和69。使用庚二烯单环氧化物70进行的模型研究导致了单保护的二羟基醛76的合成，因此建立了将加波内酯引入邻位二醇的方案。最后，将醛酸乙酸叔丁酯加到醛78中，然后进行选择性保护，脱保护和环化，完成了大环内酯85的合成。
• Remarkable Change of the Diastereoselection in the Dye-Sensitized Ene Hydroperoxidation of Chiral Alkenes by Zeolite Confinement
  作者：Manolis Stratakis、Dimitris Kalaitzakis、Dimitris Stavroulakis、Giannis Kosmas、Constantinos Tsangarakis

  DOI：10.1021/ol0352660

  日期：2003.9.1

  [GRAPHICS]The ene reaction of singlet oxygen with chiral trisubstituted alkenes bearing an alkyl and a phenyl group at the stereogenic center is erythro diastereoselective in solution and threo diastereoselective if carried out within zeolite Na-Y. The change of the diastereoselection trend by zeolite confinement is attributed to a synergism of steric effects and cation-pi interactions.
• Substrate-Directed Diastereoselective Hydroformylation: Key Step for the Assembly of Polypropionate Subunits
  作者：Bernhard Breit、Mario Dauber、Klaus Harms

  DOI：10.1002/(sici)1521-3765(19991001)5:10<2819::aid-chem2819>3.0.co;2-z

  日期：1999.10.1

  Stereoselective hydroformylation of methallylic alcohols of types 3 and 4, that employed the substrate-bound catalyst-directing ortho-diphenyl-phosphanylbenzoyl (o-DPPB) group, was used as a key step for the construction of bifunctionalized stereotriads, which ale central building blocks of polyketide natural products. The required diastereomerically pure syn- and anti- starting methallylic alcohol systems 3 and 4 were obtained either by Cram-selective carbonyl reduction, Frater alkylation, or by chelation-controlled carbonyl reduction. Enantiomerically pure stereotriad building blocks were derived from a combination of an Evans aldol addition and subsequent o-DPPB-directed stereoselective hydroformylation (-->24). A crystal structure analysis for steretriad building block 24 confirmed the relative and absolute configuration of the stereogenic centers. Additionally, it provided evidence for a previously postulated preferred conformation of the catalyst-directing o-DPPB group as well as of the polyketide main chain.