(6R)-3,6-dimethyl-5,6,7,7a-tetrahydro-2(4H)-benzofuranone | 38049-04-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (6R)-3,6-dimethyl-5,6,7,7a-tetrahydro-2(4H)-benzofuranone
• 英文别名: (-)-(1R,3R)-3,9-epoxy-p-menth-8(10)-en-9-one；(1R,3R)-3,9-oxa-9-oxo-4(8)-p-menthene；(-)-mintlactone；(R)-mintlactone；mintlactone；(-)-(6R,7aR)-5,6,7,7a-tetrahydro-3,6-dimethylbenzofuran-2(4H)-one；(6R,7aR)-3,6-dimethyl-5,6,7,7a-tetrahydro-4H-1-benzofuran-2-one
• CAS: 38049-04-6
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: VUVQBYIJRDUVHT-HZGVNTEJSA-N

物化性质

• 沸点：
  303.7±11.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)
• LogP：
  1.811 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  (6R)-3,6-dimethyl-5,6,7,7a-tetrahydro-2(4H)-benzofuranone 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到(3R,3aR,6R,7aR)-perhydro-3,6-dimethyl-2-benzo[b]furanone
  参考文献：
  名称：

  对-薄荷烷内酯的合成及感官特性

  摘要：

  描述了对-薄荷烷内酯7a - h的立体选择性合成和感官特性。除了更正有关这些化合物的公开数据外，这项工作还明确鉴定了Italo Mitcham黑色薄荷油（Mentha piperita）中的7a，7b和7g。另外，这些内酯由于其异常的气味强度和典型的香豆素样香气，在香水工业中引起了极大的兴趣。

  DOI：

  10.1016/s0040-4020(00)00397-5
• 作为产物：
  描述：

  (3R,3aS,6R,7aR)-3,6-dimethyl-3-phenylselanyl-3a,4,5,6,7,7a-hexahydro-1-benzofuran-2-one 在 双氧水 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以82%的产率得到(6R)-3,6-dimethyl-5,6,7,7a-tetrahydro-2(4H)-benzofuranone
  参考文献：
  名称：

  Total synthesis of (−)-mintlactone

  摘要：

  The first total, stereodirected synthesis of (-)-mintlactone is described. A stereoselective, radical-mediated ring closure was the key step in the synthesis.

  DOI：

  10.1016/s0040-4039(00)93463-4

文献信息

• BITTER TASTE MODIFIERS INCLUDING SUBSTITUTED 1-BENZYL-3-(1-(ISOXAZOL-4-YLMETHYL)-1H-PYRAZOL-4-YL)IMIDAZOLIDINE-2,4-DIONES AND COMPOSITIONS THEREOF
  申请人：SENOMYX, INC.

  公开号：US20160376263A1

  公开（公告）日：2016-12-29

  The present invention includes compounds and compositions known to modify the perception of bitter taste, and combinations of said compositions and compounds with additional compositions, compounds, and products. Exemplary compositions comprise one or more of the following: cooling agents; inactive drug ingredients; active pharmaceutical ingredients; food additives or foodstuffs; flavorants, or flavor enhancers; food or beverage products; bitter compounds; sweeteners; bitterants; sour flavorants; salty flavorants; umami flavorants; plant or animal products; compounds known to be used in pet care products; compounds known to be used in personal care products; compounds known to be used in home products; pharmaceutical preparations; topical preparations; cannabis-derived or cannabis-related products; compounds known to be used in oral care products; beverages; scents, perfumes, or odorants; compounds known to be used in consumer products; silicone compounds; abrasives; surfactants; warming agents; smoking articles; fats, oils, or emulsions; and/or probiotic bacteria or supplements.

  本发明涵盖已知用于改变苦味感知的化合物和组合物，以及所述组合物和化合物与额外的组合物、化合物和产品的组合。示例组合物包括以下一种或多种：冷却剂；无活性药物成分；活性药用成分；食品添加剂或食品；调味剂或调味增强剂；食品或饮料产品；苦味化合物；甜味剂；苦味剂；酸味调味剂；咸味调味剂；鲜味调味剂；植物或动物产品；已知用于宠物护理产品中的化合物；已知用于个人护理产品中的化合物；已知用于家用产品中的化合物；制药制剂；局部制剂；大麻衍生或与大麻相关的产品；已知用于口腔护理产品中的化合物；饮料；香味、香水或除臭剂；已知用于消费品中的化合物；硅化合物；磨料；表面活性剂；发热剂；吸烟物品；脂肪、油脂或乳化剂；和/或益生菌或补充剂。
• USE OF PHYSIOLOGICAL COOLING ACTIVE INGREDIENTS, AND AGENTS CONTAINING SUCH ACTIVE INGREDIENTS
  申请人：Subkowski Thomas

  公开号：US20120263659A1

  公开（公告）日：2012-10-18

  The invention relates to a TRPM8 modulator for achieving a cooling effect on the skin or a mucous membrane.

  这项发明涉及一种TRPM8调节剂，用于在皮肤或粘膜上产生降温效果。
• Synthesis of (−)‐Mintlactone via Intramolecular Wittig–Horner Reaction
  作者：Rajesh K. Pandey、Rajesh K. Upadhyay、Sandip S. Shinde、Pradeep Kumar

  DOI：10.1081/scc-120039484

  日期：2004.1.1

  Abstract An efficient synthesis of (−)‐mintlactone has been described starting from (+)‐pulegone and employing the intramolecular Wittig–Horner reaction as the key step.

  摘要 已经描述了从 (+)-胡薄荷酮开始并采用分子内 Wittig-Horner 反应作为关键步骤的 (-)-薄荷内酯的有效合成。
• COMPOUNDS USEFUL AS MODULATORS OF TRPM8
  申请人：Senomyx, Inc.

  公开号：US20170096418A1

  公开（公告）日：2017-04-06

  The present disclosure relates to compounds which are useful as cooling sensation compounds.

  本公开涉及作为冷感化合物有用的化合物。
• Efficient one-step synthesis of trialkylsubstituted 2(5H)-furanones utilizing direct Ti-crossed aldol condensation and its application to the straightforward synthesis of (R)-mintlactone and (R)-menthofuranElectronic supplementary information (ESI) available: calculated structures of 7 and 8. See http://www.rsc.org/suppdata/cc/b2/b208077j/
  作者：Yoo Tanabe、Kumi Mitarai、Takahiro Higashi、Tomonori Misaki、Yoshinori Nishii

  DOI：10.1039/b208077j

  日期：2002.10.18

  TiCl4–Bu3N-mediated condensation of ketones with α,α-dimethoxyketones afforded trialkylsubstituted 2(5H)-furanones in a one-pot manner, wherein aldol addition and furanone formation occurred sequentially; its application to straightforward synthesis of (R)-mintlactone and (R)-menthofuran, two representative natural mint perfumes, is demonstrated.

  TiCl4-Bu3N 介导的酮与α,α-二甲氧基酮的缩合以一锅方式得到了三烷基取代的 2(5H)-呋喃酮，其中醛醇加成和呋喃酮的形成依次发生；展示了其在直接合成(R)-薄荷内酯和(R)-薄荷呋喃（两种具有代表性的天然薄荷香水）中的应用。

表征谱图