2-(hydroxymethyl)-2-methyl-3,4-dihydro-2H-naphthalen-1-one | 1043892-44-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-(hydroxymethyl)-2-methyl-3,4-dihydro-2H-naphthalen-1-one
• 英文别名: (2R)-2-(hydroxymethyl)-2-methyl-3,4-dihydronaphthalen-1-one
• CAS: 1043892-44-9
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: XHJZVAQJEYCYAV-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(hydroxymethyl)-2-methyl-3,4-dihydro-2H-naphthalen-1-one 在 Geotrichum candidum (NBRC 5767) 作用下， 以 乙醇 为溶剂， 以80%的产率得到(1S,2R)-1,2,3,4-tetrahydro-2-(hydroxymethyl)-2-methylnaphthalen-1-ol
  参考文献：
  名称：

  Enantiomeric scaffolding of α-tetralone and related scaffolds by EKR (Enzymatic Kinetic Resolution) and stereoselective ketoreduction with ketoreductases

  摘要：

  基于1-四氢萘酮、1-茚酮和4-克罗莫酮骨架的立体化学纯化合物，含有全碳四元立体中心，已通过采用脂肪酶PS（来自布尔克霍尔德菌）催化的动力学分离合成。这些骨架进一步通过微生物酮还原酶（来自地霉菌、帕氏酵母和黑曲霉）进行了功能化，以获得立体化学纯的二醇，经过进一步的合成操作，得到新型环状化合物。

  DOI：

  10.1039/c1ob06545a
• 作为产物：
  描述：

  2-(羟甲基)-2-甲基-3,4-二氢萘-1-酮 在 Burkholderia cepacia lipase-PS 、 porcine pancreatic lipase 作用下， 生成 2-(hydroxymethyl)-2-methyl-3,4-dihydro-2H-naphthalen-1-one
  参考文献：
  名称：

  Enantiomeric scaffolding of α-tetralone and related scaffolds by EKR (Enzymatic Kinetic Resolution) and stereoselective ketoreduction with ketoreductases

  摘要：

  基于1-四氢萘酮、1-茚酮和4-克罗莫酮骨架的立体化学纯化合物，含有全碳四元立体中心，已通过采用脂肪酶PS（来自布尔克霍尔德菌）催化的动力学分离合成。这些骨架进一步通过微生物酮还原酶（来自地霉菌、帕氏酵母和黑曲霉）进行了功能化，以获得立体化学纯的二醇，经过进一步的合成操作，得到新型环状化合物。

  DOI：

  10.1039/c1ob06545a

文献信息

• Stereoselective Desymmetrization of 2,2-Bishydroxymethyl-1-tetralones by Iodocyclization, Synthesis of Novel Enantiopure [6.6.5] Tricyclic Framework and Chemoenzymatic Diversity Generation
  作者：Tridib Mahapatra、Navendu Jana、Samik Nanda

  DOI：10.1002/adsc.201100088

  日期：2011.8

  Stereoselective halocyclization of pro-chiral 2,2-bishydroxymethyl-1-tetralone derivatives with N-halosuccinamides afforded an interesting tricyclic scaffold found in many naturally occurring hasubanan alkaloids. Enantiopure tricyclic scaffolds are synthesized by using enzymatic kinetic resolution (EKR) of the parent racemic compound. Microbial ketoreductase (Geotrichum candidum, Aspergillus niger

  前手性2,2-双羟甲基-1-四氢萘酮衍生物与N-卤代琥珀酰胺的立体选择性卤环化作用提供了一种有趣的三​​环骨架，存在于许多天然存在的hasubanan生物碱中。通过使用母体外消旋化合物的酶促动力学拆分（EKR）合成对映体纯的三环支架。微生物酮还原酶（白地霉，黑曲霉和近平滑念珠菌）介导的立体选择性还原反应已经成功地用于这些对映体纯的三环支架其中，随后官能团操作，提供了新的环状框架。
• Chiral Scandium-Catalyzed Enantioselective Hydroxymethylation of Ketones in Water
  作者：Shū Kobayashi、Masaya Kokubo、Katsuaki Kawasumi、Takashi Nagano

  DOI：10.1002/asia.200900442

  日期：2010.3.1

  Form with formalin: Scandium‐catalyzed enantioselective hydroxymethylation of ketones has been developed using aqueous formaldehyde (formalin) in water. The addition of a catalytic amount of pyridine enables the use of ketones directly in asymmetric hydroxymethylation reactions.

  与福尔马林形成的形式：已在水中使用甲醛水溶液（福尔马林）开发了Scan催化的酮的对映体选择性羟甲基化方法。加入催化量的吡啶使得能够将酮直接用于不对称的羟甲基化反应中。
• Toward Chemistry-Based Design of the Simplest Metalloenzyme-Like Catalyst That Works Efficiently in Water
  作者：Taku Kitanosono、Shū Kobayashi

  DOI：10.1002/asia.201403004

  日期：2015.1

  artificial catalysts. Current strategies to rival enzymatic catalysis require unmodified or minimally modified structures of active sites, gigantic molecular weight, and sometimes the use of harsh conditions such as extremely low temperatures in organic solvents. Herein, we describe a design of small molecules that act as the simplest metalloenzyme‐like catalysts that can function in water, without mimicking

  与人工催化剂相比，酶具有压倒性的优越催化作用。目前与酶催化竞争的策略要求活性位点的结构未经修饰或修饰程度最低，分子量巨大，有时还需要使用苛刻的条件，例如在有机溶剂中的极低温度。本文中，我们描述了一种小分子的设计，该分子充当最简单的类似于金属酶的催化剂，可以在水中起作用，而不会模拟酶的结构。这些人造催化剂使用甲醛水溶液有效地促进了对映选择性直接型羟醛反应。反应遵循迈克尔斯-门腾动力学，并且在水中构建了耐热不对称环境。
• Enantioselective enzymatic desymmetrization of prochiral 1,3-diols and enzymatic resolution of monoprotected 1,3-diols based on α-tetralone and related multifunctional scaffolds
  作者：Tridib Mahapatra、Tapas Das、Samik Nanda

  DOI：10.1016/j.tetasy.2008.10.024

  日期：2008.11

  Novel multifunctional chemotypes based on alpha-tetralone, alpha-indarione, and chromanone have been synthesized by a chemo-enzymatic approach by applying an enzymatic irreversible transesterification strategy. The scaffolds synthesized can be further elaborated with subsequent enzymatic as well as chemical transformations for the generation of new sets of structurally related organic molecules. (C) 2008 Elsevier Ltd. All rights reserved.
• Chemoenzymatic synthesis and resolution of compounds containing a quaternary stereocenters adjacent to a carbonyl group
  作者：Tridib Mahapatra、Nandan Jana、S. Nanda

  DOI：10.1016/j.tetasy.2008.04.024

  日期：2008.5

  Racemic compounds containing a quaternary stereocenter (having hydroxymethyl and alkyl group adjacent to keto functionality) based on chromanone, alpha-tetralone, and indalone scaffolds have been synthesized. An enzymatic irreversible transesterification approach has been applied to generate the pure enantiomers in a stereocontrolled fashion. The pure enantiomers of some alpha,alpha-dialkylated carbonyl compounds have been synthesized by this method. (C) 2008 Elsevier Ltd. All rights reserved.