2,2-bis(hydroxymethyl)-3,4-dihydro-2H-naphthalen-1-one | 15121-83-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2,2-bis(hydroxymethyl)-3,4-dihydro-2H-naphthalen-1-one
• 英文别名: 2,2-bis(hydroxymethyl)-3,4-dihydronaphthalen-1(2H)-one；2,2-bis-hydroxymethyl-3,4-dihydro-2H-naphthalen-1-one；2,2-bishydroxymethyl-3,4-dihydro-2H-naphthalen-1-one；2,2-bis(hydroxymethyl)-1-tetralone；2,2-bis(hydroxymethyl)-3,4-dihydro-1(2H)-naphthalenone；2,2-bis(hydroxymethyl)-3,4-dihydronaphthalen-1-one
• CAS: 15121-83-2
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: XOCCGJHDPJDZPS-UHFFFAOYSA-N

物化性质

• 熔点：
  98-99 °C
• 沸点：
  393.3±15.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-bis(hydroxymethyl)-3,4-dihydro-2H-naphthalen-1-one 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 反应 20.0h， 以62%的产率得到2,2-bis(chloromethyl)-1-tetralone
  参考文献：
  名称：

  Spirocyclopropane Carboxylic Acids Derived from 1-Tetralone and 4-Chromanone and their Conversion to the Corresponding Pyridazinones

  摘要：

  标题化合物是由 1-四氢萘酮和 4-色萘酮合成的。根据 1H-NMR 数据确定了这两种异构体的结构和构型。

  DOI：

  10.1055/s-1990-26821
• 作为产物：
  描述：

  1H-苯并三唑-1-甲醇 、 3,4-二氢-1(2H)-萘酮 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以92%的产率得到2,2-bis(hydroxymethyl)-3,4-dihydro-2H-naphthalen-1-one
  参考文献：
  名称：

  Anionic, in Situ Generation of Formaldehyde:  A Very Useful and Versatile Tool in Synthesis

  摘要：

  A very simple, safe and powerful method for the in situ generation of formaldehyde at low temperature in anhydrous conditions is described. This new tool avoids the use of gaseous formaldehyde and is suitable for basic carbon nucleophiles which cannot be generated in aqueous reaction media. Various substrates, including organolithium reagents and enolates, underwent smooth hydroxymethylation showing the versatility of this process. A Wittig reaction was also carried out in high yield.

  DOI：

  10.1021/ol070145b

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。
• A Mild and Efficient Bisaldolization of Ketones and its Application towards Spirocyclic 1,3-Dioxanes and Novel 1,3,5-Trioxocanes
  作者：Kalpana Bhandari、Nagarapu Srinivas、Vijay Marrapu

  DOI：10.1055/s-0028-1088130

  日期：——

  Bisaldolization of aryl alkyl ketones as well as cyclic ­ketones with paraformaldehyde in the presence of a catalytic amount of l-proline and low concentration of aqueous sodium ­hydroxide has been developed in excellent yields. Further, these bisaldols are elaborated to the corresponding spirocyclic dioxanes and novel spirocyclic trioxocanes in the presence of p-toluene sulfonic acid. The structures and preferred conformations of these eight-membered spirocyclic 1,3,5-trioxocanes are discussed.

  在一定量的 l-脯氨酸和低浓度氢氧化钠水溶液催化下，芳基烷基酮和环酮与多聚甲醛发生双醛化反应，产量极佳。此外，在对甲苯磺酸的存在下，这些双醛醇还可以衍化成相应的螺环二噁烷和新型螺环三氧环。本文讨论了这些八元螺环 1,3,5-三氧杂环的结构和优选构象。
• 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.
• Anionic, in Situ Generation of Formaldehyde:  A Very Useful and Versatile Tool in Synthesis
  作者：Geoffrey Deguest、Laurent Bischoff、Corinne Fruit、Francis Marsais

  DOI：10.1021/ol070145b

  日期：2007.3.1

  A very simple, safe and powerful method for the in situ generation of formaldehyde at low temperature in anhydrous conditions is described. This new tool avoids the use of gaseous formaldehyde and is suitable for basic carbon nucleophiles which cannot be generated in aqueous reaction media. Various substrates, including organolithium reagents and enolates, underwent smooth hydroxymethylation showing the versatility of this process. A Wittig reaction was also carried out in high yield.
• Spirocyclopropane Carboxylic Acids Derived from 1-Tetralone and 4-Chromanone and their Conversion to the Corresponding Pyridazinones
  作者：Giorgio Cignarella、Daniela Barlocco、Guendalina Rossi、Elisabetta Rossi

  DOI：10.1055/s-1990-26821

  日期：——

  The title compounds were synthesized starting from 1-tetralone and 4-chromanone. Structure and configurational identification of the two isomers were assigned on the basis of 1H-NMR data.

  标题化合物是由 1-四氢萘酮和 4-色萘酮合成的。根据 1H-NMR 数据确定了这两种异构体的结构和构型。