6-methoxy-1-tetralone dithioketal | 73622-41-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 6-methoxy-1-tetralone dithioketal
• 英文别名: ethylenthioketal of 6-methoxy-α-tetralone；6'-methoxy-3',4'-dihydro-2'H-spiro[1,3-dithiolane-2,1'-naphthalene]；7'-methoxyspiro[1,3-dithiolane-2,4'-2,3-dihydro-1H-naphthalene]
• CAS: 73622-41-0
• 化学式: C₁₃H₁₆OS₂
• 分子量: 252.401
• InChiKey: WOBUPHHBFTUYIG-UHFFFAOYSA-N

物化性质

• 沸点：
  410.1±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  59.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methoxy-1-tetralone dithioketal 在 Oxone 、 potassium bromide 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以65%的产率得到6-甲氧基-1-萘满酮
  参考文献：
  名称：

  An efficient deprotection of dithioacetals to carbonyls using Oxone–KBr in aqueous acetonitrile

  摘要：

  A simple and efficient method has been developed for the chemoselective dethioacetalization of dithioacetals to aldehydes and ketones using Oxone-KBr in aqueous acetonitrile at room temperature. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.09.138
• 作为产物：
  描述：

  1,2-乙二硫醇 、 6-甲氧基-1-萘满酮 在 aluminum oxide 、 碘 作用下， 反应 0.67h， 以90%的产率得到6-methoxy-1-tetralone dithioketal
  参考文献：
  名称：

  Highly Efficient Dithioacetalization of Carbonyl Compounds Catalyzed with Iodine Supported on Neutral Alumina

  摘要：

  醛和酮在中性铝土表面上以乙炔-1,2-二硫醇的对应二硫缩醛形式得到保护，反应中使用了少量的碘作为催化剂。这是一种在温和、中性和无溶剂条件下高产率的羰基保护方法。

  DOI：

  10.1246/cl.2001.794

文献信息

• Indium triflate: a mild Lewis acid catalyst for thioacetalization and transthioacetalization
  作者：Sengodagounder Muthusamy、Srinivasarao Arulananda Babu、Chidambaram Gunanathan

  DOI：10.1016/s0040-4020(02)00897-9

  日期：2002.9

  Protection of a variety of carbonyl compounds as thioacetals using indium triflate, a mild Lewis acid catalyst, was achieved at ambient temperature in very good yield. Transthioacetalization of oxyacetals into thioacetals was also achieved in an excellent yield. A mixture of carbonyl compound and its respective oxyacetal was also completely converted into thioacetal in the presence of indium triflate. (C) 2002 Elsevier Science Ltd. All rights reserved.
• A convenient oxidative demasking of 1,3-dithiolanes and dithianes to carbonyl compounds with TBHP
  作者：Nivrutti B Barhate、Popat D Shinde、Vishal A Mahajan、Radhika D Wakharkar

  DOI：10.1016/s0040-4039(02)01210-8

  日期：2002.8

  Regeneration of carbonyl compounds from their 1,3-dithiolanes and dithianes was achieved using tert-butyl hydroperoxide (TBHP, aq. 70%) in high yields. Thus, an efficient, economic and experimentally simple protocol for dethioacetalization has been demonstrated. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Tributyltin hydride: a selective reducing agent for 1,3-dithiolanes
  作者：Carlos G. Gutierrez、Rex A. Stringham、Tadashi Nitasaka、Karl G. Glasscock

  DOI：10.1021/jo01305a004

  日期：1980.8
• GUTIEREEZ C. G.; STRINGHAM R. A.; NITASAKA T.; GLASSCOCK K. G., J. ORG. CHEM., 1980, 45, NO 17, 3393-3395
  作者：GUTIEREEZ C. G.、 STRINGHAM R. A.、 NITASAKA T.、 GLASSCOCK K. G.

  DOI：——

  日期：——
• An efficient deprotection of dithioacetals to carbonyls using Oxone–KBr in aqueous acetonitrile
  作者：U.V. Desai、D.M. Pore、B.V. Tamhankar、S.A. Jadhav、P.P. Wadgaonkar

  DOI：10.1016/j.tetlet.2006.09.138

  日期：2006.11

  A simple and efficient method has been developed for the chemoselective dethioacetalization of dithioacetals to aldehydes and ketones using Oxone-KBr in aqueous acetonitrile at room temperature. (c) 2006 Elsevier Ltd. All rights reserved.