(R)-(-)-1-methyl-1,2,3,4-tetrahydronaphthalen-1yl acetate | 1130108-70-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (R)-(-)-1-methyl-1,2,3,4-tetrahydronaphthalen-1yl acetate
• 英文别名: (R)-(−)-1-methyl-1,2,3,4-tetrahydronaphthalen-1-yl acetate；[(1R)-1-methyl-3,4-dihydro-2H-naphthalen-1-yl] acetate
• CAS: 1130108-70-1
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: NJRQQBIFWFSVCZ-CYBMUJFWSA-N

物化性质

• 沸点：
  278.3±19.0 °C(predicted)
• 密度：
  1.07±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3,4-二氢-1(2H)-萘酮 在 Candida antarctica Lipase A 作用下， 以 乙醚 为溶剂， 反应 27.5h， 生成 (S)-(+)-1-methyl-1,2,3,4-tetrahydronaphthalen-1-ol 、 (R)-(-)-1-methyl-1,2,3,4-tetrahydronaphthalen-1yl acetate
  参考文献：
  名称：

  叔醇的动态动力学拆分。

  摘要：

  尽管动态动力学拆分对于多种化合物类别都取得了巨大的成功，但叔醇及其相应的酯仍然是这类方法最具挑战性的底物之一。这是由于叔醇的大小和位阻以及由于难于寻找使这些化合物消旋化的反应条件同时与拆分反应相容的原因，优选用酶进行。在这项研究中，提出了外消旋叔醇动力学动力学拆分的第一个例子。通过将脂肪酶催化的动力学拆分与利用生物相容性氧钒催化剂的原位外消旋相结合，可以实现所需对映体纯酯的合成。第一，检查，改进和调整了两个单独的反应，使其彼此兼容。随后，将两种催化剂按定制量添加导致所需的组合过程，并以＞ 99％的ee和超过50％的转化率递送产物，从而证明了这种所需的叔醇动力学动力学分辨率。

  DOI：

  10.1039/c9cc09103c

文献信息

• Optically active tertiary alcohols by biocatalysis
  作者：Devrim Özdemirhan

  DOI：10.1080/00397911.2016.1274032

  日期：2017.4.3

  chemoenzymatic route to optically active aromatic ring-fused cyclic tertiary alcohols (S)-(–)-1-methyl-1,2,3,4-tetrahydronaphthalen-1-ol-(–)-1b, (S)-(+)-1-methyl-2,3-dihydro-1H-inden-1-ol-(+)-1a has been reported.[9] CAL-A (lipase-A from Candida antarctica) was found the best biocatalyst for 1b, CAL-A cross linked enzyme aggregate (CLEA) for 1a, with ee values of 20 and 45% and the esters 2b and 2a with ee values

  摘要 最初，化学酶法制备光学活性芳香环稠环叔醇 (S)-(–)-1-methyl-1,2,3,4-tetrahydronaphthalen-1-ol-(–)-1b, (S) -(+)-1-methyl-2,3-dihydro-1H-inden-1-ol-(+)-1a 已有报道。[9] CAL-A（来自南极念珠菌的脂肪酶-A）被发现是 1b 的最佳生物催化剂，CAL-A 交联酶聚集体 (CLEA) 是 1a 的 ee 值为 20% 和 45%，酯 2b 和 2a 的 ee 值为 99和 71%。然后，环戊二烯锚定的叔烯丙基 1a'、高烯丙基 1b' 和高炔丙基 1c 醇以高 ee（高达 90%）进行酶促拆分，化学收率分别为 44%、40% 和 43%，环己基 2 -ene 在高 ee（高达 97%）中锚定叔烯丙基 3a、高烯丙基 3b 和高炔丙基 3c 醇，化学产率依次为 42%、45% 和
• Enzyme-catalyzed resolution of aromatic ring fused cyclic tertiary alcohols
  作者：Devrim Özdemirhan、Serdar Sezer、Yasemin Sönmez

  DOI：10.1016/j.tetasy.2008.12.002

  日期：2008.12

  An efficient chemoenzymatic route for the synthesis of optically active aromatic ring fused cyclic tertiary alcohols (S)-(-)-1-methyl-1,2,3,4-tetrahydronaphthalen-1-ol (-)-1b and (S)-(+)-1-methyl-2,3-dihydro-1H-inden-1-ol (+)-1a has been developed. Different lipases have been tested in the transesterification of these tertiary alcohols; CAL-A (Candida antarctica Lipase A) was found to be the best biocatalyst for 1b and CAL-A-CLEA (Lipase A, C. antarctica, cross-linked enzyme aggregate) for la, obtained with ee values of 20% and 45%, respectively, and the corresponding esters 2b and 2a with the ee values of 99% and 71%, respectively. (C) 2008 Elsevier Ltd. All rights reserved.
• Enzymatic Kinetic Resolution of Tertiary Benzyl Bicyclic Alcohols: Studies of the Reaction Conditions for a More Efficient Protocol
  作者：Laiza de Almeida、Laerte Ganéo Neto、Cintia Milagre、Humberto Milagre

  DOI：10.21577/0103-5053.20240033

  日期：——

  The reactivity and steric hindrance of optically active tertiary alcohols limit the development of more direct enantioselective methodologies for their synthesis, such as kinetic resolution (KR). In this work, we optimized the reaction conditions of an enzymatic KR of two tertiary benzyl bicyclic alcohols using readily available reagents and biocatalyst. Studies were conducted with 1-methyl-1,2,3,4-tetrahydronaphthalen-1-ol and 1-methyl-2,3-dihydro-1H-inden-1-ol as substrates and commercial lipase A from Candida antarctica (CAL-A) as biocatalyst for the enantioselective transesterification of these racemic tertiary alcohols. After varying the reaction parameters, such as acyl donor, solvent, and enzyme/substrate ratio, the (R)-esters were obtained with high conversions (44-45%) and excellent enantiomeric excess (96-99%) in only 4-5 h, to our knowledge being the best result for KR of the evaluated tertiary alcohols in terms of reaction rate, conversion, and enantioselectivity reported so far.