(R)-2-羟基-2-苯基丙醛 | 69489-14-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (R)-2-羟基-2-苯基丙醛
• 英文名称: (S)-(+)-2-hydroxy-2-phenylpropanal
• 英文别名: (2S)-2-Hydroxy-2-phenylpropanal；(S)-2-hydroxy-2-phenylpropanal；(S)-(+)-2-hydroxy-2-phenylpropionaldehyde；α-Phenyl-α-hydroxy-propionaldehyd
• CAS: 69489-14-1
• 化学式: C₉H₁₀O₂
• 分子量: 150.177
• InChiKey: DJSCQCGHDWBAMG-SECBINFHSA-N

物化性质

• 沸点：
  250.6±28.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-羟基-2-苯基丙醛 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 (2S)-2-phenylpropane-1,2-diol
  参考文献：
  名称：

  N -boc恶唑烷类化合物不对称合成高手性1,2-二醇

  摘要：

  由苯乙二醛和乙醛酸乙酯合成非对映异构纯的N -Boc 2-酰基氧唑烷。这些杂环与格氏试剂的反应是高度立体选择性的。在N-脱保护，水解和还原中间体α-羟基醛之后，最终获得手性1,2-二醇。不对称诱导可以通过螯合模型来解释。

  DOI：

  10.1016/s0040-4039(00)76893-6
• 作为产物：
  描述：

  (1S,2R,3S,5R,2'R)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane 在 N-氯代丁二酰亚胺 、 silver nitrate 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 生成 (R)-2-羟基-2-苯基丙醛
  参考文献：
  名称：

  Enantioselective synthesis of either enantiomer of α-alkyl-α-hydroxy-α-phenylacetic acids using chiral auxiliaries

  摘要：

  The enantioselective synthesis of either enantiomer of of alpha-alkyl-alpha-hydroxy-alpha-phenylacetic acids was achieved by using 2-acyloxathianes 1a-c and the mixed acyl-S,O-acetals 7 and 8 as chiral auxiliaries, which can straightforwardly be prepared from (1R)-(-)-myrtenal. This procedure allowed the preparation of the title compounds in >95% enantiomeric excess (ee). (C) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2005.03.032

文献信息

• Highly enantioselective syntheses of α-hydroxyacids using N-benzyl-4,4,7α-trimethyl--octahydro-1, 3-benzoxazine as a chiral adjuvant
  作者：Xu-Chang He、Ernest L. Eliel

  DOI：10.1016/s0040-4020(01)87677-8

  日期：1987.1

  Addition of Grignard and organolithium reagents to as well as hydride reduction of 2α-benzoyl-N-benzyl-4,4,7α-trimethyl--octahydro-1 ,3-benzoxazine (2, Y = C6H5CO) and addition of phenylmagnesium bromide to the corresponding 2-acetyl analog (11) proceed in highly diastereoselective fashion to produce virtually exclusively the diastereomer predicted on the basis of Cram's chelate rule if chelation involves

  添加格氏试剂和有机锂试剂，以及将2α-苯甲酰基-N-苄基-4,4,7α-三甲基-八氢-1,3-苯并恶嗪（2，Y = C 6 H 5 CO）氢化还原并添加如果螯合涉及环氧原子，则将苯基溴化镁与相应的2-乙酰基类似物（11）进行高非对映选择性的方式，实际上仅产生根据克拉姆螯合规则预测的非对映异构体。加合物的轻度酸水解，然后进行选择性氧化，可生成高对映体纯的对羟基酸，并且可以干净地回收手性佐剂。
• Me ₂ Zn‐Mediated Catalytic Enantio‐ and Diastereoselective Addition of TosMIC to Ketones
  作者：Abdul Raheem Keeri、Andrea Gualandi、Andrea Mazzanti、Janusz Lewinski、Pier Giorgio Cozzi

  DOI：10.1002/chem.201504362

  日期：2015.12.21

  The first catalytic asymmetric addition of TosMIC to unactivated ketones is presented. A combination of Me2Zn and aminoalcohol catalyst promoted the aldol addition/cyclization reaction to render oxazolines possessing a fully substituted stereocenter with excellent yields (up to 92 %), high enantioselectivities (up to 96 %), and complete diastereoselectivity. The chiral oxazolines were then used to

  提出了将TosMIC首次催化不对称加成至未活化的酮中。Me 2 Zn和氨基醇催化剂的结合促进了羟醛的加成/环化反应，使恶唑啉具有完全取代的立体中心，具有极好的收率（高达92％），高的对映选择性（高达96％）和完全的非对映选择性。在直接酸水解后，手性恶唑啉然后用于在不消旋的情况下，得到带有叔醇基序（例如羟醛，羟酸和羟酸酯）的对映体富集的结构单元。
• Asymmetric syntheses based on 1,3-oxathianes. 2. Synthesis of chiral tertiary .alpha.-hydroxy aldehydes, .alpha.-hydroxy acids, glycols [R1R2C(OH)CH2OH], and carbinols [R1R2C(OH)Me] in high enantiomeric purity.
  作者：Joseph E. Lynch、Ernest L. Eliel

  DOI：10.1021/ja00322a034

  日期：1984.5

  Scission par le N-chlorosuccinimide de trimethyl-4,4,7 oxa-1thia-3 bicyclo [4.4.0] decanecarbinols, avec formation d'α-aldols. Etude de l'oxydation et de la reduction de ces α-aldols

  Scission par le N-chlorosuccinimide de trimethyl-4,4,7 oxa-1thia-3 双环 [4.4.0] 癸烷醇，avec 形成 d'α-醛醇。α-醛醇的氧化和还原练习曲
• .alpha.-Hydroxyaldehyde and a process for preparing the same
  申请人：Sumitomo Chemical Company, Limited

  公开号：US04337346A1

  公开（公告）日：1982-06-29

  An optically active or racemic .alpha.-hydroxyaldehyde represented by the general formula (2), ##STR1## wherein R.sub.1 represents a C.sub.6 -C.sub.14 aryl group, C.sub.1 -C.sub.10 alkyl group, C.sub.3 -C.sub.10 alkenyl group, C.sub.2 -C.sub.10 alkynyl group, C.sub.7 -C.sub.14 aralkyl group, or a group containing a functional group in the organic portion of said groups and R.sub.2 represents a C.sub.1 -C.sub.10 alkyl group, C.sub.2 -C.sub.10 alkenyl group, C.sub.2 -C.sub.10 alkynyl group, C.sub.7-C.sub.14 aralkyl group, C.sub.6 -C.sub.14 aryl group, or a group containing a functional group in the organic portion of these groups, which is an important intermediate for preparation of pharmaceuticals and agricultural chemicals, and prepared by allowing an optically active or racemic compound represented by the general formula (1), ##STR2## (wherein A represents a C.sub.6 -C.sub.14 aryl group or a C.sub.1 -C.sub.4 alkyl or alkoxy group- or halogen-substituted C.sub.6 -C.sub.14 aryl group and R.sub.1 is as defined above) to react with a Grignard reagent, and thereafter hydrolyzing the reaction product.

  一种光学活性或拉氏体的α-羟基醛，由通式（2）表示，其中R₁代表C₆-C₁₄芳基、C₁-C₁₀烷基、C₃-C₁₀烯基、C₂-C₁₀炔基、C₇-C₁₄芳基烷基或含有有机部分中的官能团的基团，R₂代表C₁-C₁₀烷基、C₂-C₁₀烯基、C₂-C₁₀炔基、C₇-C₁₄芳基烷基、C₆-C₁₄芳基或含有这些基团的有机部分中的官能团的基团，这是制备药物和农药的重要中间体，通过让通式（1）表示的光学活性或拉氏体化合物（其中A代表C₆-C₁₄芳基或C₁-C₄烷基或烷氧基-或卤素取代的C₆-C₁₄芳基，R₁如上定义）与格氏试剂反应，然后水解反应产物制备而成。
• Enantioselective alkynylation of carbonyl compounds with trimethoxysilylalkynes catalyzed by lithium binaphtholate
  作者：Tomohiro Ueda、Kana Tanaka、Tomonori Ichibakase、Yuya Orito、Makoto Nakajima

  DOI：10.1016/j.tet.2010.07.080

  日期：2010.9

  Enantioselective alkynylation of aldehydes and ketones was accomplished using trimethoxysilylalkynes as alkynylating reagents and lithium 3,3′-diphenylbinaphtholate as a catalyst. Optically active propargylic alcohols were obtained in good to high chemical yields and enantioselectivities. Alkynylation of acetylpyridines afforded biologically active pyridyl propargylic alcohols in good enantioselectivities

  使用三甲氧基甲硅烷基炔烃作为炔基化试剂和3,3'-二苯基联萘甲酸锂实现对醛和酮的对映选择性炔基化。以良好至高的化学产率和对映选择性获得了光学活性的炔丙醇。乙酰吡啶的炔基化得到具有良好对映选择性的生物活性吡啶基炔丙基醇。