(4-phenylcyclohexyl) acetate | 5445-95-4

• 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: (4-phenylcyclohexyl) acetate
• 英文别名: acetic acid,4-phenylcyclohexan-1-ol；trans-4-phenylcyclohexyl acetate；trans-4-Phenylcyclohexylacetat
• CAS: 5445-95-4；68285-52-9；55122-66-2
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: BPTLOURWNCPYTR-HDJSIYSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

安全信息

• 海关编码：
  2915390090

反应信息

• 作为反应物：
  描述：

  (4-phenylcyclohexyl) acetate 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以62%的产率得到4-PHENYLCYCLOHEXANOL
  参考文献：
  名称：

  Karamysheva, L. A.; Torgova, S. I.; Agafonova, I. F., Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 5.1, p. 736 - 741

  摘要：

  DOI：
• 作为产物：
  描述：

  4-acetylcyclohexylbenzene 在 甲酸 、 双氧水 作用下， 反应 4.0h， 以100%的产率得到(4-phenylcyclohexyl) acetate
  参考文献：
  名称：

  Karamysheva, L. A.; Torgova, S. I.; Agafonova, I. F., Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 5.1, p. 736 - 741

  摘要：

  DOI：

文献信息

• A Facile and Efficient One-Step Conversion of Alcohol Triphenylmethyl Ethers to the Corresponding Acetates
  作者：Takeshi Oriyama、Kumiko Kobayashi、Tsutomu Watahiki

  DOI：10.1055/s-2003-37641

  日期：——

  Alcohol triphenylmethyl (trityl) ethers were readily and efficiently transformed into the corresponding acetates by reaction with acetyl bromide. Triphenylmethyl ethers can also be transformed into the corresponding substituted acetates in high yields by the use of various substituted acetyl chlorides combined with sodium iodide.

  醇三苯甲基（三苯甲基）醚通过与乙酰溴反应容易且有效地转化为相应的乙酸酯。通过使用各种取代的乙酰氯与碘化钠结合，三苯甲基醚也可以高产率地转化为相应的取代乙酸酯。
• Improved Process for the Palladium-Catalyzed C–O Cross-Coupling of Secondary Alcohols
  作者：Hong Zhang、Paula Ruiz-Castillo、Alexander W. Schuppe、Stephen L. Buchwald

  DOI：10.1021/acs.orglett.0c01668

  日期：2020.7.17

  An improved protocol for the Pd-catalyzed C–O cross-coupling of secondary alcohols is described. The use of biaryl phosphine L2 as the ligand was key to achieving efficient cross-coupling of (hetero)aryl chlorides with only a 20% molar excess of the alcohol. Additionally, we observed an unusual reactivity difference between an electron-rich aryl bromide and the analogous aryl chloride, and deuterium-labeling

  描述了一种用于Pd催化仲醇交叉偶联的改进方案。使用联芳基膦L 2作为配体是实现（杂）芳基氯与仅20摩尔摩尔过量的醇的有效交叉偶联的关键。此外，我们观察到富电子的芳基溴化物与类似的芳基氯之间存在异常的反应性差异，氘标记表明当前未确定的还原途径在解释这种差异中起重要作用。
• Potential antiinflammatory agents. IV. Stereoselective synthesis of 6-chloro-5-(3'- and 4'-hydroxycyclohexyl)indan-1-carboxylic acids related to metabolites of 6-chloro-5-cyclohexylindan-1-carboxylic acid (TAI-284).
  作者：SHOJI KISHIMOTO、TETSUYA AONO、YOSHIAKI ARAKI、ISAO MINAMIDA、KUNIHIRO TANAKA、SHUNSAKU NOGUCHI

  DOI：10.1248/cpb.22.2231

  日期：——

  In the course of synthetic study of metabolites of a new potent antiinflammatory agent, 6-chloro-5-cyclohexylindan-1-carboxylic acid (TAI-284), 5-(cis-and trans-3'-hydroxy-cyclohexyl) indan-1-carboxylic acids (25 and 26) and 5-(cis- and trans-4'-hydroxycyclohexyl) indan-1-carboxylic acids (17 and 16) were stereoselectively prepared by sodium borohydride reduction (equatorial alcohol formation) and catalytic hydrogenation (axial alcohol formation) of the corresponding 3'-oxo and 4'-oxo compounds (24 and 15), respectively. Chlorination of 25, 26, 17 and 16 with molecular chlorine in acetonitrile gave their 6-chloro derivatives (27, 28, 21 and 20), which were correlated with metabolites of TAI-284. Of these indans, 3'-hydroxy compounds (25-28) were prepared as a pair of racemic diastereoisomers.

  在合成研究一种新型强效抗炎剂--6-氯-5-环己基茚满-1-羧酸（TAI-284）的代谢物的过程中、通过硼氢化钠还原相应的 3'-氧代和 4'-氧代化合物（24 和 15）（形成赤道醇）和催化加氢（形成轴醇），分别立体选择性地制备了 5-（顺式和反式-3'-羟基-环己基）茚满-1-羧酸（25 和 26）和 5-（顺式和反式-4'-羟基-环己基）茚满-1-羧酸（17 和 16）。在乙腈中用分子氯将 25、26、17 和 16 氯化，得到了它们的 6-氯衍生物（27、28、21 和 20），这些衍生物与 TAI-284 的代谢物有关。在这些茚满物中，3'-羟基化合物（25-28）是以一对外消旋非对映异构体的形式制备的。
• Iron-catalysed cross-coupling of halohydrins with aryl aluminium reagents: a protecting-group-free strategy attaining remarkable rate enhancement and diastereoinduction
  作者：Shintaro Kawamura、Tatsuya Kawabata、Kentaro Ishizuka、Masaharu Nakamura

  DOI：10.1039/c2cc34185a

  日期：——

  Non-protected halohydrins are cross-coupled with aryl aluminium reagents to produce aryl alkanols in the presence of the iron–bisphosphine catalysts. Remarkable reaction rate enhancement and diastereoinduction are realized by the in situ generated aluminium alkoxides, offering a new method for the reactivity and selectivity control of the iron-catalysed cross-coupling reaction.

  在铁-双膦催化剂存在下，未保护的卤代醇与芳基铝试剂交叉偶联生成芳基烷醇。原位生成的铝醇盐实现了显着的反应速率提高和非对映诱导，为铁催化交叉偶联反应的反应性和选择性控制提供了新方法。
• A one-step and chemoselective conversion of silyl-protected alcohols into the corresponding acetates
  作者：Takeshi Oriyama、Mihoko Oda、Junko Gono、Gen Koga

  DOI：10.1016/s0040-4039(00)73040-1

  日期：1994.3

  A reagent system of acetyl bromide combined with a catalytic amount of tin(II) bromide cleaves readily trialkylsilyl ethers to give the corresponding acetates in high yields under very mild conditions.