(R)-octan-2-yl 4-bromobenzoate | 132247-95-1

• 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: (R)-octan-2-yl 4-bromobenzoate
• 英文别名: [(2R)-octan-2-yl] 4-bromobenzoate
• CAS: 132247-95-1
• 化学式: C₁₅H₂₁BrO₂
• 分子量: 313.235
• InChiKey: RODLDJINWHATIF-GFCCVEGCSA-N

物化性质

• 沸点：
  365.0±15.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-octan-2-yl 4-bromobenzoate 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 sodium hydride 、 三苯基膦 作用下， 以 三乙胺 、 甲苯 、 paraffin 为溶剂， 生成 (4-nonoxyphenyl) 4-[2-[4-[(2R)-octan-2-yl]oxycarbonylphenyl]ethynyl]benzoate
  参考文献：
  名称：

  手性 Tolans：铁电液晶的新系列。合成和介晶性质

  摘要：

  通过钯催化偶联反应合成的具有手性烷基的二苯乙炔同系物提供了一系列新的液晶材料，其形成具有铁电性质的手性近晶 C (SmC*) 相。由三个芳环组成的化合物的介晶性质受炔键位置和酯键单元方向的强烈影响。已经系统地研究了末端链长的变化对近晶 A (SmA) 和 SmC* 两个和三个芳环系统的热稳定性的影响。

  DOI：

  10.1246/bcsj.63.1020
• 作为产物：
  描述：

  1-辛炔 在 C₃₈H₄₆O₃P₂*C₇H₈*Rh⁽¹⁺⁾*BF₄^(1-) 、 氢气 、 钌 作用下， 以 二氯甲烷 、 水 为溶剂， 40.0~60.0 ℃ 、400.01 kPa 条件下， 反应 48.0h， 生成 (R)-octan-2-yl 4-bromobenzoate
  参考文献：
  名称：

  1-烷基乙烯基苯甲酸酯的高度对映选择性加氢：手性2-烷基醇的简单，非酶促途径

  摘要：

  走向手性！描述了通过使用带有P bearingOP配体的Rh催化剂对烯醇酯1的高度对映选择性催化氢化（参见方案； NBD ＝降冰片二烯）。该催化体系具有广泛的范围，并允许制备具有高对映选择性的各种带有各种烷基或苄基的手性酯2。这些酯可以很容易地转化为高度对映体富集的2-链烷醇。

  DOI：

  10.1002/chem.201303500

文献信息

• Nucleophilic Substitution Reactions of (Alkoxymethylene)dimethylammonium Chloride
  作者：Anthony G. M. Barrett、D. Christopher Braddock、Rachel A. James、Nobuyuki Koike、Panayiotis A. Procopiou

  DOI：10.1021/jo980583j

  日期：1998.9.1

  The use of imidate esters as potential replacements for diethyl azodicarboxylate and triphenylphosphine in the Mitsunobu reaction is described. A series of secondary alcohols were allowed to react with (chloromethylene)dimethylammonium chloride, generated from dimethylformamide (DMF) and oxalyl chloride, to give imidate esters. Reaction of these salts with potassium benzoate or potassium phthalimide

  描述了在Mitsunobu反应中使用亚氨酸酯作为偶氮二羧酸二乙酯和三苯基膦的潜在替代物。使一系列仲醇与由二甲基甲酰胺（DMF）和草酰氯生成的（氯亚甲基）二甲基氯化铵反应，得到亚氨酸酯。这些盐与苯甲酸钾或邻苯二甲酰亚胺钾的反应以极好的收率得到了S（N）2取代的产物，且立体化学清晰易懂。讨论了反应条件的优化，作为通过减少所需亲核试剂的量来增加该方法的原子经济性的手段。
• Microwave-Assisted Acylation of Amines, Alcohols, and Phenols by the Use of Solid-Supported Reagents (SSRs)
  作者：Elena Petricci、Claudia Mugnaini、Marco Radi、Federico Corelli、Maurizio Botta

  DOI：10.1021/jo048837q

  日期：2004.11.1

  A microwave-assisted synthesis of solid-supported reagents for the acylation of amines has been developed, and the same methodology has been successfully applied to the preparation of acylating agents anchored on different solid supports. Similarly, alcohols, phenols, and thiophenols have been easily acylated using these reagents under microwave irradiation.

  已经开发了微波辅助的用于胺的酰化的固体负载试剂的合成，并且相同的方法已经成功地应用于制备锚定在不同固体载体上的酰化剂。类似地，使用这些试剂在微波辐射下很容易将醇，酚和硫酚酰化。
• Asymmetric Hydrogenation of 1-Alkyl and 1-Aryl Vinyl Benzoates: A Broad Scope Procedure for the Highly Enantioselective Synthesis of 1-Substituted Ethyl Benzoates
  作者：Patryk Kleman、Pedro J. González-Liste、Sergio E. García-Garrido、Victorio Cadierno、Antonio Pizzano

  DOI：10.1021/cs501402z

  日期：2014.12.5

  The enantioselective hydrogenation of enol esters of formula CH2=C(OBz)R with rhodium catalysts based on phosphine phosphite ligands (P-OP) has been studied. The reaction has a broad scope, and it is suitable for the preparation of products possessing a wide variety of R substituents. For the cases where R is a primary alkyl, high catalyst activity (S/C = 500) and enantioselectivities (95-99% ee) were obtained with a catalyst characterized by an ethane backbone and a PPh2 fragment. In contrast, for R = t-Bu, a catalyst possessing a benzene backbone provided the best results (97% ee). Derivatives with a cycloalkyl R substituent were particularly difficult substrates for this reaction. A broader catalyst screening was required for these substrates, which identified a catalyst possessing a P(m-xylyl)(2) fragment as the most appropriate one, affording enantioselectivities between 90 and 95% ee. Outstanding enantioselectivities (99% ee) and high catalyst activity (S/C = 500-1000) were also obtained in the case of substrates bearing a Ph or a fluoroaryl R substituent. In addition, the system is also appropriate for the preparation of other synthetically useful esters as those for R = benzyl, 2-phenylethyl or N-phthalimido alkyl chains. Likewise, the hydrogenation of divinyl dibenzoates proceeded with very high diastero- and enantioselectivity, generating rather low amounts of the meso isomer (3-6%). On the other hand, substrates with Br and MeO substituents at the phenyl benzoate ring, suitable for further functionalization, have also been examined. The results obtained indicate no detrimental effect of these substituents in the hydrogenation. Alternatively, the methodology has been applied to the highly enantioselective synthesis of deuterium isotopomers of 1-octyl benzoate bearing CDH2, CD2H, or CD3 fragments. Finally, as a practical advantage of the present system, it has been observed that the high performance of the catalysts is retained in highly concentrated solutions or even in the neat substrate, minimizing both the amount of solvent added and the volume of the reaction.