syn-2-ethyl-1-phenylpropane-1,3-diol

• 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: syn-2-ethyl-1-phenylpropane-1,3-diol
• 英文别名: (1R,2S)-2-ethyl-1-phenylpropane-1,3-diol
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: LASLKQCWKBYAIZ-GXSJLCMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  syn-2-ethyl-1-phenylpropane-1,3-diol 在 三丁基膦 、 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,3R)-3-ethyl-2-phenylselenetane
  参考文献：
  名称：

  Formation of Selenetanes from 2-(3-Hydroxyalkylseleno)-benzoxazoles

  摘要：

  DOI：

  10.3987/com-97-s(n)45
• 作为产物：
  描述：

  2-(hydroxymethyl)-1-phenylbutan-1-one 以95%的产率得到syn-2-ethyl-1-phenylpropane-1,3-diol
  参考文献：
  名称：

  通过氢化钠和氢化硼锂的钛醇化物高度非对映选择性还原α-烷基-β-羟基酮

  摘要：

  α-烷基-β羟基酮的还原是高顺式-选择性如果在THF中用的LiBH进行他们的Ti-醇化物配合物4或三仲丁基硼氢化锂®或N- selectride ®取决于组的键合于该蓬松性羰基。

  DOI：

  10.1016/s0040-4039(99)00308-1

文献信息

• Highly diastereoselective reduction of α-alkyl-β-hydroxy ketones with sodium and lithium boron hydrides via their titanium alcoholates
  作者：Giuseppe Bartoli、M.Cristina Bellucci、Marcella Bosco、Renato Dalpozzo、Enrico Marcantoni、Letizia Sambri

  DOI：10.1016/s0040-4039(99)00308-1

  日期：1999.4

  The reduction of α-alkyl-β-hydroxy ketones is highly syn-selective if carried out in THF on their Ti-alcoholate complexes with LiBH4 or L-Selectride® or N-selectride® depending on the bulkiness of the group bound to the carbonyl group.

  α-烷基-β羟基酮的还原是高顺式-选择性如果在THF中用的LiBH进行他们的Ti-醇化物配合物4或三仲丁基硼氢化锂®或N- selectride ®取决于组的键合于该蓬松性羰基。
• Rhodium-Catalyzed Cross-Aldol Reaction: In Situ Aldehyde-Enolate Formation from Allyloxyboranes and Primary Allylic Alcohols
  作者：Luqing Lin、Kumiko Yamamoto、Shigeki Matsunaga、Motomu Kanai

  DOI：10.1002/anie.201205680

  日期：2012.10.8

  Dip in! A Rh/dippf catalyst generates aldehyde‐derived enol boranes at ambient temperature by isomerization of allyloxy‐ and homoallyloxyboranes. A one‐pot isomerization/cross‐aldol sequence provides aldehyde–aldehyde adducts in good yield with syn selectivity. Direct use of primary allylic and homoallylic alcohols was also achieved.

  蘸！Rh / dippf催化剂在环境温度下通过烯丙氧基和高烯丙氧基硼烷的异构化反应生成醛衍生的烯醇硼烷。的单釜异构化/交-羟醛序列提供以良好的收率与醛的醛加成物合成 的选择性。还实现了直接使用伯烯丙基和均烯丙基醇。
• Rh-Catalyzed AldehydeAldehyde Cross-Aldol Reaction under Base-Free Conditions: In Situ Aldehyde-Derived Enolate Formation through Orthogonal Activation
  作者：Luqing Lin、Kumiko Yamamoto、Shigeki Matsunaga、Motomu Kanai

  DOI：10.1002/asia.201300928

  日期：2013.12

  The chemoselective generation of aldehyde‐derived enolates to realize an aldehydealdehyde cross‐aldol reaction is described. A combined Rh/dippf system efficiently promoted the isomerization/aldol sequence by using primary allylic, homoallylic, and bishomoallylic alcohols; secondary allylic and homoallylic alcohols; and trialkoxyboranes that were derived from primary allylic and homoallylic alcohols

  描述了实现醛醛交叉醇醛缩合反应的醛基烯醇化物的化学选择性生成。Rh / dippf组合系统通过使用伯烯丙基，均烯丙基和双烯丙基烯丙醇有效地促进了异构化/羟醛序列。仲烯丙基和均烯丙基醇；以及衍生自伯烯丙基和均烯丙基醇的三烷氧基硼烷。该反应在无碱条件下于环境温度下进行，因此得到具有高化学选择性的交叉羟醛产物。还描述了机理研究及其在无保护基团条件下在双羟醛工艺中的应用。
• Preparation of 2-(3-Hydroxyalkylthio)benzoxazoles and their Conversion into Thietanes
  作者：Dai Ikemizu、Ayako Matsuyama、Kazunori Takemura、Oyo Mitsunobu

  DOI：10.1055/s-1997-1032

  日期：1997.11

  Reaction of primary or secondary 1,3-diols with dibenzoxazol-2-yl disulfide and tributylphosphine or triphenylphosphine selectively gave 2-(3-hydroxyalkylthio)benzoxazoles which, on treatment with KH, were converted into the corresponding thietanes. 2,2-Dibenzylthietane-1-oxide reacted with silylated purines and pyrimidines in the presence of TMSOTf and ZnI2 to give the corresponding thietane nucleosides in 17-69% yields.

  初级或次级1,3-二醇与二苯并噻唑-2-基二硫和三丁基磷或三苯基磷的反应选择性地生成2-(3-羟基烷基硫)苯并噻唑，在与氢化钾处理后转化为相应的硫杂环己烷。2,2-二苯基硫杂环己烷-1-氧化物在TMSOTf和ZnI2的存在下与硅化嘌呤和嘧啶反应，得到相应的硫杂环核苷，收率为17-69%。
• Copper-Catalyzed Stereospecific Hydroboration of Internal Allylic Alcohols
  作者：Enhui Ji、Haiwen Meng、Yue Zheng、Velayudham Ramadoss、Yahui Wang

  DOI：10.1002/ejoc.201901435

  日期：2019.11.30

  Copper‐catalyzed highly stereospecific hydroboration of internal allylic alcohols using a silyl ether transient protection strategy is reported. This in situ protection effectively avoids the preferential side reaction of free hydroxyl group with boron reagent, thus promoting hydroboration. This method provides both the anti‐ and the syn‐ diastereomers of 1,3‐diols in high level of diastereomeric ratios

  据报道，使用甲硅烷基醚瞬态保护策略，铜催化内部烯丙基醇的高度立体定向氢硼化。这种原位保护有效地避免了游离羟基与硼试剂的优先副反应，从而促进了硼氢化反应。此方法同时提供抗-和SYN在高电平非对映体比率具有官能团的耐受性良好的1,3-二醇非对映体- 。