(S)-3-氰基-2-甲基-1-丙醇四氢吡喃醚 | 88557-55-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 中文名称: (S)-3-氰基-2-甲基-1-丙醇四氢吡喃醚
• 英文名称: (S)-(-)-4-hydroxy-3-methylbutanenitrile THP ether
• 英文别名: (S)-(-)-3-methyl-4-<(2-tetrahydropyranyl)oxy>butyronitrile；(3S)-3-methyl-4-(oxan-2-yloxy)butanenitrile
• CAS: 88557-55-5；110171-23-8；143900-00-9；143900-08-7
• 化学式: C₁₀H₁₇NO₂
• 分子量: 183.25
• InChiKey: AZWSYGNSEHXDBG-RGURZIINSA-N

物化性质

• 沸点：
  310.0±37.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-氰基-2-甲基-1-丙醇四氢吡喃醚 在 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 20.0h， 以86%的产率得到(S)-4-hydroxy-3-methylbutanenitrile
  参考文献：
  名称：

  Synthesis of chiral building blocks using Pseudomonas Fluorescens lipase catalyzed asymmetric hydrolysis of Meso diacetates

  摘要：

  Two chiral building blocks were prepared using a lipase-catalyzed asymmetric hydrolysis of the corresponding meso-diacetates. The chirality in the hydrolyzed products was conveniently incorporated into that of (R)-muscone and hunger modulator.

  DOI：

  10.1016/s0957-4166(00)80142-1
• 作为产物：
  描述：

  (2S)-2-甲基-3-(四氢吡喃-2-氧基)丙烷-1-醇 以 吡啶 、 二甲基亚砜 为溶剂， 反应 3.5h， 生成 (S)-3-氰基-2-甲基-1-丙醇四氢吡喃醚
  参考文献：
  名称：

  Total Synthesis of (−)-Ircinianin and (+)-Wistarin

  摘要：

  (-)-Ircinianin (1)，一种从海海绵（Ircinia属）中分离出的环状糠酸酯倍半萜四烯酸，通过(S)-2-甲基丙烷-1,3-二醇单THP醚(10)和3-糠醛在17步反应中合成。关键步骤涉及在DMSO中，NiCl₂-CrCl₂介导的碘代三烯(9)与手性醛(8)之间的偶联反应，随后在同一锅中进行分子内Diels-Alder反应。这两个反应在室温下进行得非常顺利，最终以60%的收率得到环状产物30A，其具有目标化合物1所需的环状骨架。通过X射线晶体学分析确定了30A的结构。讨论了Diels-Alder反应中7A和另一个非环前体7B的立体化学。通过1和碘醚环的形成以及碘化物33A的氢解，首次完成了(+)-wistarin (2)的全合成，产率为55%。根据33A的¹H NMR光谱中的偶合常数，对报道的结构2A进行了修订，最终结构为2B。

  DOI：

  10.1021/jo961993f

文献信息

• A facile synthesis of (–)-muscone using a chemo-enzymatic approach
  作者：Zhuo-Feng Xie、Hiroshi Suemune、Kiyoshi Sakai

  DOI：10.1039/c39880001638

  日期：——

  Pseudomonas fluorescens lipase catalysed hydrolysis of the meso-diacetate (1) to give specifically the (R)-enantiomer (2) with high optical purity allows the synthesis of (–)-muscone in combination with a three-carbon ring expansion.

  荧光假单胞菌脂肪酶催化内消旋二乙酸酯（1）水解，得到具有高光学纯度的（R）-对映异构体（2），可以合成（-）-muscone和三碳环扩环。
• Axially Chiral 1,7-Naphthyridine-6-carboxamide Derivatives as Orally Active Tachykinin NK₁ Receptor Antagonists:  Synthesis, Antagonistic Activity, and Effects on Bladder Functions
  作者：Hideaki Natsugari、Yoshinori Ikeura、Izumi Kamo、Takenori Ishimaru、Yuji Ishichi、Akira Fujishima、Toshimasa Tanaka、Fumiko Kasahara、Mitsuru Kawada、Takayuki Doi

  DOI：10.1021/jm990220r

  日期：1999.9.1

  Cyclic analogues of N-[3,5-bis(trifluoromethyl)benzyl]-7,8-dihydro-N,7-dimethyl-5-(4-methylphenyl)-8-oxo-1,7-naphthyridine-6-carboxamide (1) having a 6-9-membered ring (6-9) were synthesized and evaluated for NK1 antagonistic activities. The 8-membered ring compound with a beta-methyl group at the C-(9)-position, (aR,9R)-7-[3,5-bis(trifluoromethyl)benzyl]-8,9,10,-11-tetrahydro-9-methyl-5-(4-methylphenyl)-7H-[1,4]diazocino[2,1-g][1,7]naphthyridine-6,13-di-one [(aR,9R)-8b], was atropodiastereoselectively synthesized by cyclization of a chiral intermediate, 10g. On the other hand, the 7-membered ring compound with a beta-methyl group at the C-(9)-position [(9S)-7b] was obtained as an equilibrium mixture of atropisomers with a ratio of ca. 3:2 in solution at room temperature (measured by NMR in CDCl3). Compounds (9S)-7b and (aR,9R)-8b exhibited excellent antagonistic activities both in vitro [IC50 (inhibition of [I-125]BH-SP binding in human IM-9 cells) = 0.28 and 0.45 nM, respectively] and in vivo (iv and po). Significantly, the in vitro activity of (aR,9R)-8b was ca. 750-fold higher than that of its enantiomer (aS,9S)-8b, ca. 40-fold higher than its atropisomer (aS,9R)-8b, and ca. 20-fold higher than its diastereomer (aR,9S)-8b. The structure-activity relationships in this series, along with the X-ray analysis of (aR,9R)-8b, indicated that the stereochemistry around the -C-(6)(=O)-N-(7)-CH2Ar moiety is important for NK1 receptor recognition. The NK1 antagonists showed effects on bladder functions in guinea pigs upon intravenous injection: i.e., the antagonists increased the shutdown time of distension-induced rhythmic bladder contractions and the bladder volume threshold, and the effects on the shutdown time were found to correlate well with the NK1 antagonistic activities. Compound (aR,9R)-8b has been identified as a potential clinical candidate for the treatment of bladder function disorders.
• Revision of the absolute configuration of a-factor
  作者：Kenji Mori

  DOI：10.1016/s0040-4020(01)91552-2

  日期：1983.1
• XIE, ZHUO-FENG;SUEMUNE, HIROSHI;SAKAI, KLYOSHI, J. CHEM. SOC. CHEM. COMMUN.,(1988) N 24, C. 1638-1639
  作者：XIE, ZHUO-FENG、SUEMUNE, HIROSHI、SAKAI, KLYOSHI

  DOI：——

  日期：——
• Synthesis of chiral building blocks using Pseudomonas Fluorescens lipase catalyzed asymmetric hydrolysis of Meso diacetates
  作者：Zhuo-Feng Xie、Hiroshi Suemune、Kiyoshi Sakai

  DOI：10.1016/s0957-4166(00)80142-1

  日期：1993.5

  Two chiral building blocks were prepared using a lipase-catalyzed asymmetric hydrolysis of the corresponding meso-diacetates. The chirality in the hydrolyzed products was conveniently incorporated into that of (R)-muscone and hunger modulator.