rac-3-acetoxy-1-phenylpropan-1-ol | 62296-03-1

• 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: rac-3-acetoxy-1-phenylpropan-1-ol
• 英文别名: 3-acetoxy-1-phenyl-propan-1-ol；3-Acetoxy-1-phenyl-propanol-(1)；3-Hydroxy-3-phenylpropylacetat；1-Phenyl-3-acetoxy-propanol-(1)；1-Phenyl-3-acetoxy-1-propanol；(3-Hydroxy-3-phenylpropyl) acetate
• CAS: 62296-03-1
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: FFWXGONOKFRRKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  rac-3-acetoxy-1-phenylpropan-1-ol 在 chromium(VI) oxide 、 盐酸 、 溶剂黄146 作用下， 生成 3-羟基-1-苯基丙烷-1-酮
  参考文献：
  名称：

  Reaction of 4-Phenyl-1,3-dioxane with Acetic Anhydride

  摘要：

  DOI：

  10.1021/jo01093a040
• 作为产物：
  描述：

  苯甲酰乙酸乙酯 在 sodium tetrahydroborate 、 C_. antarctica B immobilized lipase 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 11.0h， 生成 rac-3-acetoxy-1-phenylpropan-1-ol
  参考文献：
  名称：

  宝石-二乙酸酯作为酒精酶促区域选择性和立体选择性酰化的替代试剂的评估

  摘要：

  双乙酸双乙酸酯已被用作可持续的酰基供体，用于手性和非手性醇的酶促酰化。特别是，据透露，孪位二乙酸酯表现出比对于对乙醛敏感水解乙酸乙烯酯反应性更高。在优化的酶促酰化条件下，可以以高达98％的极高收率获得几种合成相关的各种伯醇的饱和和不饱和乙酸酯，而无需双键的E / Z异构化。随后，从所得的醛中重新生成酰基供体，并在酰化中不断重复使用。因此，所开发的方法的特征在于高原子效率。此外，还显示了使用双子胺的酰化作用通过区分1-苯基-1,3-丙二醇中的伯羟基和仲羟基，二乙酸酯可产生显着的区域选择性，从而以高收率仅提供3-乙酰氧基-1-苯基-丙烷-1-醇。此外，酶动力学拆分（EKR）和酶化学动态动力学拆分（DKR）协议使用被开发偕二乙酸作为酰化剂，产生的手性乙酸盐以高收率高达94％与对映体过量超过99％。

  DOI：

  10.1021/acs.joc.1c00154

文献信息

• Reactions of silver(<scp>I</scp>) acetate–iodine and thallium(<scp>I</scp>) acetate–iodine with substituted cyclopropanes
  作者：Peter H. Atkinson、Richard C. Cambie、Graham Dixon、Wendy I. Noall、Peter S. Rutledge、Paul D. Woodgate

  DOI：10.1039/p19770000230

  日期：——

  Treatment of phenylcyclopropane with silver(I) acetate–iodine or thallium(I) acetate–iodine gives, as the major products, 1,3-disubstituted phenylpropanes resulting from cyclopropane ring opening, and in some cases, from solvolysis of intermediate iodo-acetates. Similar products are given with silver(I) trifluoroacetate–iodine but in this case aromatic iodination also occurs. Treatment of norcarane

  用乙酸碘化银（I）或乙酸碘化th（I）处理苯基环丙烷，作为主要产物，是由环丙烷开环以及某些情况下由中间碘代乙酸盐的溶剂化产生的1,3-二取代苯基丙烷。三氟乙酸银（I）-碘也可提供类似的产品，但在这种情况下也会发生芳族碘化。用相同的试剂处理正二十烷也会导致开环，但此处的副产物是通过消除和随后添加而产生的。两种底物对烯烃对每种试剂的反应性均不如烯烃。讨论了反应机理。据报道其他涉及亲电碘与苯基环丙烷和正戊烷的试剂系统的作用。
• Selective Oxidation of Alcohols with Alkali Metal Bromides as Bromide Catalysts: Experimental Study of the Reaction Mechanism
  作者：Katsuhiko Moriyama、Misato Takemura、Hideo Togo

  DOI：10.1021/jo5008064

  日期：2014.7.3

  A bromide-catalyzed oxidation of alcohols was developed which proceeded in the presence of an alkali metal bromide and an oxidant under mild conditions. The reaction involved an organic-molecule-free oxidation using KBr and Oxone and a Brønsted acid assisted oxidation using KBr and aqueous H2O2 solution to provide a broad range of carbonyl compounds in high yields. Moreover, the bromide-catalyzed oxidation

  开发了溴化物催化的醇的氧化反应，该氧化反应在碱金属溴化物和氧化剂的存在下于温和的条件下进行。该反应涉及使用KBr和Oxone进行无有机分子的氧化，以及使用KBr和H 2 O 2水溶液进行布朗斯台德酸辅助氧化，以高收率提供各种羰基化合物。而且，在TEMPO存在下，在两种反应条件下，溴化物催化的伯醇的氧化使得羧酸和醛的发散合成成为可能。在各种机理研究的基础上，提出了一种可能的催化机理。
• Method of preparing (S)-1-phenyl-1,3-propanediol or derivatives thereof
  申请人：Ajinomoto Co., Inc.

  公开号：EP0542300A2

  公开（公告）日：1993-05-19

  (S)-1phenyl-1,3-propanediol or a derivative thereof having high optical purity can be produced simply in high yield, by contacting 1-phenylpropan-3-ol-1-one with a culture of microorganisms, microorganism cells isolated from the culture, or a product obtainable by processing the microorganism cells.

  (S)-1-苯基-1,3-丙二醇或其具有高光学纯度的衍生物，可以通过将 1-苯基-3-丙醇-1-酮与微生物培养物、从培养物中分离出的微生物细胞或通过加工微生物细胞获得的产品接触而简单高产地生产出来。
• Optically active phenol derivatives and preparation thereof
  申请人：TAKEDA CHEMICAL INDUSTRIES, LTD.

  公开号：EP0582382A2

  公开（公告）日：1994-02-09

  An optically active tri-substituted methane compound having, as substituents, an aromatic ring group and a phenyl group having hydroxyl group at ortho or para position can be obtained by allowing a phenol compound unsubstituted at the ortho- or/and para-position to react with an optically active secondary carbinol compound having an aromatic ring group at the alpha-position in the presence of tri-substituted phosphine and diazodicarboxylate or diazodicarboxamide. These and other optically active tri-substituted methane compounds are useful as active ingredients for medicines or as intermediate compounds for preparing medicines.

  在三取代膦和重氮二羧酸盐或重氮二甲酰胺的存在下，使在正位或/和对位上未被取代的苯酚化合物与在α位上具有芳香环基的光学活性仲甲醇化合物反应，可得到光学活性三取代甲烷化合物，其取代基为芳香环基和在正位或对位上具有羟基的苯基。这些和其他具有光学活性的三取代甲烷化合物可用作药物的活性成分或制备药物的中间化合物。
• Cobalt(II) chloride catalyzed acylation of alcohols with acetic anhydride: scope and mechanism
  作者：Javed Iqbal、Rajiv Ranjan Srivastava

  DOI：10.1021/jo00033a020

  日期：1992.3

  Cobalt(II) chloride catalyzes the acetylation of a variety of alcohols with acetic anhydride in excellent yield. Primary hydroxyl groups can be selectively acylated in the presence of secondary and tertiary ones while the secondary hydroxyl groups can be preferentially acetylated in the presence of tertiary ones. Tertiary alcohols have been found to give ketones, acetoacetates, olefins, and diketene in addition to the acetate. The beta-hydroxy esters and ketones can be acylated under these conditions without any elimination, and this reaction has been compared with 4-(dimethylamino)pyridine (DMAP)-mediated acylations where elimination of the resulting beta-acetoxy carbonyl compound is observed. A detailed investigation of the acylation of tertiary alcohols has revealed that these reactions proceed via a tertiary alkoxy radical and ketene. A mechanism for these acylations is proposed by invoking an electron-transfer process.