(2-bromo-3,5-dimethylphenyl)methanol | 1000990-17-9

• 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: (2-bromo-3,5-dimethylphenyl)methanol
• 英文别名: 2-bromo-3,5-dimethylbenzylalcohol；2-Bromo-3,5-dimethylbenzenemethanol
• CAS: 1000990-17-9
• 化学式: C₉H₁₁BrO
• 分子量: 215.09
• InChiKey: LNOYOGYSVRBOEZ-UHFFFAOYSA-N

物化性质

• 熔点：
  58-60 °C
• 沸点：
  295.4±35.0 °C(Predicted)
• 密度：
  1.415±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2-bromo-3,5-dimethylphenyl)methanol 在 4 A molecular sieve 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以84%的产率得到2-bromo-3,5-dimethylbenzaldehyde
  参考文献：
  名称：

  Photoinduced C−Br Homolysis of 2-Bromobenzophenones and Pschorr Ring Closure of 2-Aroylaryl Radicals to Fluorenones

  摘要：

  [Graphics]A variety of diversely substituted 2-aroylaryl radicals, generated by photoinduced homolysis of 2-bromoarylketones, is shown to undergo Pschorr cyclization to yield fluorenones in moderate to excellent yields. The photochemical results illustrate that the substituents in the two phenyl rings of the 2-bromobenzophenone skeleton exert a dramatic influence on the reactivity of the derived 2-aroylaryl radicals. The disubstitution by methoxy groups in the radical ring renders the aryl sigma-radical highly electrophilic and unreactive for hydrogen abstraction and cyclization. On the other hand, the substituents in the non-radical ring that strongly stabilize the hydrofluorenyl pi-radical, formed subsequent to the attack of the 2-aroylaryl radical on the non-radical ring, promote cyclization to furnish fluorenones in excellent isolated yields.

  DOI：

  10.1021/jo7017872
• 作为产物：
  描述：

  2-bromo-3,5-dimethyl-benzoic acid 在 N,N'-羰基二咪唑 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.33h， 以49%的产率得到(2-bromo-3,5-dimethylphenyl)methanol
  参考文献：
  名称：

  Kawabata, Takeo; Jiang, Changsheng; Hayashi, Kazuhiro, Journal of the American Chemical Society, 2009, vol. 131, p. 54 - 55

  摘要：

  DOI：

文献信息

• The total synthesis of the cybrodins
  作者：William A. Ayer、Robert H. McCaskill

  DOI：10.1139/v81-311

  日期：1981.7.15

  The total syntheses of cybrodol (1), isocybrodol (2), cybrodal (3), cybrodic acid (4), and trisnorcybrodolide (5), starting from 2-bromomesitylene (6) are described. The route involves oxidation of the 5-methyl group of 6 by means of chromyl acetate, addition of the β-hydroxyethyl chain by aryllithiation and reaction with ethylene oxide, and addition of the fifth carbon substituent by aryllithiation and treatment with ethyl chloroformate to give the key intermediate, methyl 3-(2-hydroxyethyl)-6-methoxymethyl-2,4-dimethylbenzoate (18d). The latter was transformed into trisnorcybrodolide (5), and further elaborated via the corresponding aldehyde 21 into the remaining cybrodins.

  本文描述了从2-溴二甲苯（6）出发，合成环孢多醇（1）、异环孢多醇（2）、环孢醇（3）、环孢酸（4）和三降环孢内酯（5）的总过程。该路线涉及通过铬酰醋酸氧化6的5-甲基团，通过芳基锂化和与环氧乙烷反应添加β-羟乙基链，并通过芳基锂化和用氯甲酸乙酯处理添加第五个碳取代基，得到关键中间体，即甲基3-(2-羟乙基)-6-甲氧甲基-2,4-二甲基苯甲酸酯（18d）。后者被转化为三降环孢内酯（5），并通过相应的醛21进一步细化成剩余的环孢素。
• Mechanistic Switch via Subtle Ligand Modulation: Palladium-Catalyzed Synthesis of α,β-Substituted Styrenes via CH Bond Functionalization
  作者：Areli Flores-Gaspar、Ruben Martin

  DOI：10.1002/adsc.201100140

  日期：2011.5

  new catalyst system able to efficiently perform the synthesis of styrenes via CH bond functionalization and a subtle ligand modification are described. The high level of activity achieved allows for the synthesis of highly functionalized α,β‐substituted styrenes, even the elusive E‐configured trisubstituted olefins, in a regio‐ and stereoselective manner. Mechanistic experiments allowed for the identification

  能够有效地进行苯乙烯的合成的新的催化剂体系通过Ç  H键官能化和微妙的配位基修饰的描述。所获得的高活性可以以区域和立体选择性的方式合成高度官能化的α，β取代的苯乙烯，甚至是难以捉摸的E构型的三取代烯烃。机理实验允许鉴定相应的合成中间体。
• Photoinduced C−Br Homolysis of 2-Bromobenzophenones and Pschorr Ring Closure of 2-Aroylaryl Radicals to Fluorenones
  作者：Jarugu Narasimha Moorthy、Subhas Samanta

  DOI：10.1021/jo7017872

  日期：2007.12.1

  [Graphics]A variety of diversely substituted 2-aroylaryl radicals, generated by photoinduced homolysis of 2-bromoarylketones, is shown to undergo Pschorr cyclization to yield fluorenones in moderate to excellent yields. The photochemical results illustrate that the substituents in the two phenyl rings of the 2-bromobenzophenone skeleton exert a dramatic influence on the reactivity of the derived 2-aroylaryl radicals. The disubstitution by methoxy groups in the radical ring renders the aryl sigma-radical highly electrophilic and unreactive for hydrogen abstraction and cyclization. On the other hand, the substituents in the non-radical ring that strongly stabilize the hydrofluorenyl pi-radical, formed subsequent to the attack of the 2-aroylaryl radical on the non-radical ring, promote cyclization to furnish fluorenones in excellent isolated yields.
• [EN] ESTROGEN RECEPTOR MODULATORS<br/>[FR] MODULATEURS DE RECEPTEUR D'OESTROGENES
  申请人：MERCK & CO INC

  公开号：WO2004073612A2

  公开（公告）日：2004-09-02

  The present invention relates to compounds and derivatives thereof, their synthesis, and their use as estrogen receptor modulators. The compounds of the instant invention are ligands for estrogen receptors and as such may be useful for treatment or prevention of a variety of conditions related to estrogen functioning including: bone loss, bone fractures, osteoporosis, metastatic bone disease, Paget s disease, periodontal disease, cartilage degeneration, endometriosis, uterine fibroid disease, hot flashes, increased levels of LDL cholesterol, cardiovascular disease, impairment of cognitive functioning, cerebral degenerative disorders, restenosis, gynecomastia, vascular smooth muscle cell proliferation, obesity, incontinence, and cancer.
• Kawabata, Takeo; Jiang, Changsheng; Hayashi, Kazuhiro, Journal of the American Chemical Society, 2009, vol. 131, p. 54 - 55
  作者：Kawabata, Takeo、Jiang, Changsheng、Hayashi, Kazuhiro、Tsubaki, Kazunori、Yoshimura, Tomoyuki、et al.

  DOI：——

  日期：——