methyl 2,3-diphenyl-2-hydroxypropanate | 83026-52-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: methyl 2,3-diphenyl-2-hydroxypropanate
• 英文别名: 2-Hydroxy-2,3-diphenyl-propionic acid methyl ester；methyl 2-hydroxy-2,3-diphenylpropanoate
• CAS: 83026-52-2
• 化学式: C₁₆H₁₆O₃
• mdl: MFCD15832995
• 分子量: 256.301
• InChiKey: PAKVGKHUEOAAIK-UHFFFAOYSA-N

物化性质

• 熔点：
  86-87 °C
• 沸点：
  380.9±37.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.187
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2,3-diphenyl-2-hydroxypropanate 在 盐酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 72.0h， 生成 2-hydroxy-2,3-diphenylpropionic acid isopropyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of Z-α-Aryl-α,β-unsaturated Esters

  摘要：

  An efficient method for the stereoselective synthesis of (Z)-alpha- arylacrylates is described. Treatment of alpha-hydroxyesters with triflic anhydride and pyridine at 0 C followed by warming to room temperature afforded the corresponding (Z)-alpha-aryl-alpha,beta-unsaturated esters in very good yields and excellent stereoselectivity.

  DOI：

  10.1021/jo060586t
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 水 、 sodium nitrite 作用下， 生成 methyl 2,3-diphenyl-2-hydroxypropanate
  参考文献：
  名称：

  Antispasmodics. I. Basic Esters of Some Arylacetic Acids¹

  摘要：

  DOI：

  10.1021/ja01242a036

文献信息

• Alpha,beta-unsaturated esters and acids by stereoselective dehydration
  申请人：Deng Xiaohu

  公开号：US20060004195A1

  公开（公告）日：2006-01-05

  There are provided by the present invention certain pyrazole based CCK-1 receptor modulators which have the general formula: wherein Ar is an aromatic or heteroaromatic group, X is a hydrocarbon linker, Y is a bond or hydrocarbon linker and R 1 , R 2 , R 3 , R 4 and R 5 are certain organic substituents, methods for making the same, and stereoselective dehydration methods for generally making α,β-unsaturated esters, acids and their derivatives.

  本发明提供了一些基于吡唑的CCK-1受体调节剂，其具有以下一般式： 其中Ar是芳香族或杂环芳基，X是碳氢链，Y是键或碳氢链，R1、R2、R3、R4和R5是某些有机取代基，以及制备这些化合物的方法，以及用于通常制备α，β-不饱和酯，酸及其衍生物的立体选择性脱水方法。
• Carbon–carbon bond formation via benzoyl umpolung attained by photoinduced electron-transfer with benzimidazolines
  作者：Tomohito Igarashi、Eiji Tayama、Hajime Iwamoto、Eietsu Hasegawa

  DOI：10.1016/j.tetlet.2013.10.028

  日期：2013.12

  A photoreaction between benzoyl compounds, such as benzoylformate derivatives, and 2-(p-anisyl)-1,3-dimethylbenzimidazoline in the presence of allyl bromide was found to give various allylated alcohols. In the reaction of benzoylformates, α-hydroxy ester enolates, for which the negative charge occurs on the carbonyl carbon of benzoyl (umpolung reactivity), are proposed to be generated as intermediates

  发现在烯丙基溴的存在下，苯甲酰基化合物如苯甲酰基甲酸酯衍生物与2-（对茴香基）-1，3-二甲基苯并咪唑啉之间的光反应产生了各种烯丙基化的醇。在苯甲酰基甲酸酯的反应中，建议通过苯并咪唑啉向光激发的苯甲酰基甲酸酯的电子转移，作为中间体生成α-羟基酯烯酸酯，其在苯甲酰基的羰基碳上带有负电荷。这些物质与烯丙基溴反应生成α-烯丙基-α-羟基酯。
• Photo-allylation and photo-benzylation of carbonyl compounds using organotrifluoroborate reagents
  作者：Yutaka Nishigaichi、Takayuki Orimi、Akio Takuwa

  DOI：10.1016/j.jorganchem.2009.08.011

  日期：2009.11

  Allyl- and benzyl-trifluoroborates can be applied to the photoreaction of carbonyl compounds to afford the corresponding alcoholic adducts in acceptable yields via a photo-induced single electron transfer pathway. The results were confirmed from the reaction selectivity and the negative free energy change for the electron transfer process.

  可以将三氟硼酸烯丙酯和苄基三氟硼酸酯通过光诱导的单电子转移途径以可接受的收率用于羰基化合物的光反应，以提供相应的醇加合物。从反应选择性和电子转移过程的负自由能变化中证实了该结果。
• Visible-Light-Catalyzed Radical–Radical Cross-Coupling Reaction of Benzyl Trifluoroborates and Carbonyl Compounds to Sterically Hindered Alcohols
  作者：Hao-Luo Jiang、Yu-Hao Yang、Yan-Hong He、Zhi Guan

  DOI：10.1021/acs.orglett.2c01583

  日期：2022.6.17

  require any external oxidants or reductants. In this reaction, benzyl trifluoroborates are oxidized by excited-state 4Cz-IPN to generate benzyl radicals, and the resulting boron trifluoride acts as a Lewis acid to reduce the reduction potential of carbonyl compounds. The dual roles of benzyl trifluoroborates enable aldehydes, ketones, diketones, and ketone esters to react with benzyl trifluoroborates to

  我们在此报告了一种基于持久自由基效应 (PRE) 的有机染料催化的直接自由基交叉偶联反应，该反应由可见光驱动，不需要任何外部氧化剂或还原剂。在该反应中，三氟硼酸苄酯被激发态 4Cz-IPN 氧化生成苄基自由基，生成的三氟化硼作为路易斯酸降低羰基化合物的还原电位。三氟硼酸苄酯的双重作用使醛、酮、二酮和酮酯能够与三氟硼酸苄酯反应生成各种位阻醇。
• Substituted phenyl-2-propenoic acid derivatives and their use as fungicides
  申请人：ZENECA LIMITED

  公开号：EP0260794A2

  公开（公告）日：1988-03-23

  Compounds of formula (I): and stereoisomers thereof, wherein X, Y and Z, which are the same or different, are hydrogen, halogen, hydroxy, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aralkyl, optionally substituted arylalkoxy, optionally substituted aryloxyalkyl, optionally substituted acyloxy, optionally substituted amino, acylamino, nitro, cyano, -CO₂R¹, -CONR²R³, or -COR⁴, or X and Y, when they are in adjacent positions on the phenyl ring, join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; W is a C-linked optionally substituted six membered heterocyclic ring other than pyrimidinyl, containing two to four nitrogen atoms, and wherein adjacent substituents may together form a fused aromatic or hetero-aromatic ring; A is oxygen or sulphur; and R¹, R², R³ and R⁴, which are the same or different, are hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkynyl, optionally substituted aryl or optionally substituted aralkyl; or metal complexes thereof. The compounds are useful fungicides.

  式(I)化合物： 及其立体异构体，其中相同或不同的 X、Y 和 Z 为氢、卤素、羟基、任选取代的烷基、任选取代的烯基、任选取代的芳基、任选取代的炔基、任选取代的烷氧基、任选取代的芳氧基、任选取代的芳烷基、任选取代的芳烷氧基、任选取代的芳烷氧基、任选取代的芳氧基烷基、任选取代的芳烷氧基、任选取代的芳烷氧基、任选取代的芳氧基烷基、任选取代的酰氧基、任选取代的氨基、酰氨基、硝基、氰基、-CO₂、任选取代的芳氧基烷基、任选取代的酰氧基、任选取代的氨基、酰氨基、硝基、氰基、-CO₂R¹、-CONR²R³ 或 -COR⁴，或当 X 和 Y 位于苯基环上的相邻位置时，连接形成一个融合环，可以是芳香族或脂肪族，任选含有一个或多个杂原子；W 是除嘧啶基以外的 C 键任选取代的六成员杂环，含有二至四个氮原子，其中相邻取代基可共同形成一个融合的芳香族或杂芳环；A 是氧或硫；以及 R¹、R²、R³ 和 R⁴（相同或不同）是氢、烷基、环烷基、环烷基烷基、烯基、炔基、任选取代的芳基或任选取代的芳烷基；或其金属络合物。这些化合物是有用的杀真菌剂。