2-乙酰基-5-甲基苯甲腈 | 64113-87-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-乙酰基-5-甲基苯甲腈
• 英文名称: 4-Acetyl-3-cyanotoluol
• 英文别名: 2-acetyl-5-methylbenzonitrile
• CAS: 64113-87-7
• 化学式: C₁₀H₉NO
• 分子量: 159.188
• InChiKey: KQALDXSZMFIDOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-乙酰基-5-甲基苯甲腈 在 sodium tetrahydroborate 、 盐酸 、 水 作用下， 以 甲醇 、 水 为溶剂， 反应 48.5h， 以73%的产率得到3,6-dimethylisobenzofuran-1(3H)-one
  参考文献：
  名称：

  Highly Stereoselective Chemoenzymatic Synthesis of the 3H-Isobenzofuran Skeleton. Access to Enantiopure 3-Methylphthalides

  摘要：

  A straightforward synthesis of (S)-3-methylphthalides has been developed, with the key asymmetric step being the bioreduction of 2-acetylbenzonitriles. Enzymatic processes have been found to be highly dependent on the pH value, with acidic conditions being required to avoid undesired side reactions. Baker's yeast was found lobe the best biocatalyst acting in a highly stereoselective fashion. The simple treatment of the reaction crudes with aqueous HCl has provided access to enantiopure (S)-3-methylphthalides in moderate to excellent yields.

  DOI：

  10.1021/ol300191s
• 作为产物：
  描述：

  4-甲基-2-硝基苯甲酸 在 盐酸 、 二氧化铂 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 乙二醇二甲醚 、 乙二醇二乙醚 、 水 为溶剂， 反应 7.08h， 生成 2-乙酰基-5-甲基苯甲腈
  参考文献：
  名称：

  Highly Stereoselective Chemoenzymatic Synthesis of the 3H-Isobenzofuran Skeleton. Access to Enantiopure 3-Methylphthalides

  摘要：

  A straightforward synthesis of (S)-3-methylphthalides has been developed, with the key asymmetric step being the bioreduction of 2-acetylbenzonitriles. Enzymatic processes have been found to be highly dependent on the pH value, with acidic conditions being required to avoid undesired side reactions. Baker's yeast was found lobe the best biocatalyst acting in a highly stereoselective fashion. The simple treatment of the reaction crudes with aqueous HCl has provided access to enantiopure (S)-3-methylphthalides in moderate to excellent yields.

  DOI：

  10.1021/ol300191s

文献信息

• REMEDY FOR OSTEOPOROSIS AND DIAZEPINE COMPOUND
  申请人：YOSHITOMI PHARMACEUTICAL INDUSTRIES, LTD.

  公开号：EP0638560A1

  公开（公告）日：1995-02-15

  A remedy for osteoporosis containing a diazepine compound represented by general formula (I) or a pharmaceutically acceptable salt thereof as the active ingredient; a method of treating osteoporosis by administering the above compound; and the use of the compound for preparing a remedy for osteoporosis in formula (I) Ar represents aryl or heteroaryl; X represents oxygen or sulfur; W represents -N(R³⁶)-, -O- or -S-; Q represents a ring selected among (a), (b), (c) and (d), X and Y may be combined together to form =N-N=C(R⁶)-, =N-C(R⁵)=C(R⁶)-, =C(R⁵)-N=C(R⁶)-, =N-O-CO- or =N-N(R⁵)-CO-.

  一种治疗骨质疏松症的药物，含有通式(I)代表的二氮杂卓化合物或其药学上可接受的盐作为活性成分；一种通过施用上述化合物治疗骨质疏松症的方法；以及该化合物用于制备骨质疏松症药物的用途，在式(I)中 Ar 代表芳基或杂芳基；X代表氧或硫； W代表-N(R³⁶)-、-O-或-S-；Q 代表选自(a)、(b)、(c)和(d)的环，X 和 Y 可结合在一起形成 =N-N=C(R⁶)-、=N-C(R⁵)=C(R⁶)-、=C(R⁵)-N=C(R⁶)-、=N-O-CO- 或 =N-N(R⁵)-CO-。
• US5593988A
  申请人：——

  公开号：US5593988A

  公开（公告）日：1997-01-14
• US5753649A
  申请人：——

  公开号：US5753649A

  公开（公告）日：1998-05-19
• Highly Stereoselective Chemoenzymatic Synthesis of the 3<i>H</i>-Isobenzofuran Skeleton. Access to Enantiopure 3-Methylphthalides
  作者：Juan Mangas-Sánchez、Eduardo Busto、Vicente Gotor-Fernández、Vicente Gotor

  DOI：10.1021/ol300191s

  日期：2012.3.16

  A straightforward synthesis of (S)-3-methylphthalides has been developed, with the key asymmetric step being the bioreduction of 2-acetylbenzonitriles. Enzymatic processes have been found to be highly dependent on the pH value, with acidic conditions being required to avoid undesired side reactions. Baker's yeast was found lobe the best biocatalyst acting in a highly stereoselective fashion. The simple treatment of the reaction crudes with aqueous HCl has provided access to enantiopure (S)-3-methylphthalides in moderate to excellent yields.