1-Butanol, 2-methyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]-, (2R,3S)-rel- | 65781-36-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 1-Butanol, 2-methyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]-, (2R,3S)-rel-
• 英文别名: 1-Butanol, 2-methyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]-, (2S,3S)-；(2S,3R)-2-methyl-3-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)butan-1-ol；(2R,3S)-2-methyl-3-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)butan-1-ol；(2S,3S)-2-methyl-3-((tetrahydropyran-2-yl)oxy)butan-1-ol；(2S,3S)-2-methyl-3-(2-tetrahydropyranyloxy)butanol
• CAS: 65781-36-4；65830-35-5；65830-36-6；84621-64-7；108815-13-0；129830-50-8
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: PQLRCOXRPYWNKF-KYHHOPLUSA-N

物化性质

• 沸点：
  306.3±32.0 °C(predicted)
• 密度：
  1.00±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-Butanol, 2-methyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]-, (2R,3S)-rel- 以 吡啶 为溶剂， 生成 erythro-(2S,3S,7S)-3,7-dimethylpentadecan-2-ol
  参考文献：
  名称：

  Syntheses of the Sex-Attractant of Pine Sawflies

  摘要：

  为了确定不同种类松锯齿蝇性引诱剂的立体化学结构，合成了(2S,3R,7R)-、(2S,3R,7S)-和(2S,3S,7S)-2-乙酰氧基和 2-丙酰氧基-3,7-二甲基十五烷。每种信息素的醇分子都是通过 C12 嵌段的格氏试剂与 C5 嵌段的甲苯磺酸盐偶联制备的。C12 嵌段(R)-和(S)-1-溴-2-甲基十一烷是由(R)-(+)-pulegone 制备的。(2R,3S)-或(2S,3S)-2-甲基-3-四氢吡喃氧基-1-(对甲苯磺酰氧基)丁烷等 C5 嵌段是由(2S,3S)-或(2R,3S)-2-甲基-3-羟基丁酸在不对称改性镍催化剂上通过 2-甲基-3-氧代丁酸甲酯的对映异构加氢反应制备的。

  DOI：

  10.1246/bcsj.57.1954
• 作为产物：
  描述：

  (1'R,2'S)-2'-(N-benzyl-N-mesitylenesulfonyl)amino-1'-phenyl-1'-propyl (2R,3S)-3-((tetrahydropyran-2-yl)oxy)-2-methylbutyrate 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 以94%的产率得到1-Butanol, 2-methyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]-, (2R,3S)-rel-
  参考文献：
  名称：

  Total synthesis of diastereomeric marine butenolides possessing a syn-aldol subunit at C10 and C11 and the related C11-ketone

  摘要：

  Two diastereomeric marine butenolides. (4S,10R,11R)- and (4S,10S,11S)-4,11-dihydroxy-10-methyldodec2-en-1,4-olide, possessing a syn-aldol subunit at C10 and C11 have been efficiently synthesized by using a three-module coupling strategy. The enantiomeric syn-aldol modules prepared by the syn-selective aldol reaction of the norephedrine-derived chiral propionates were coupled with the chiral C3-C7 module via 1,3-dithiane bisalkylation. The butenolide ring was then installed via a high-yielding ring-closing metathesis (RCM) reaction. Oxidation of the diastereomeric C11-alcohols furnished the corresponding C11-ketones, which are produced by the same marine microorganism. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.115

文献信息

• A Flexible Stereocontrolled Synthesis of β-Hydroxy-α-methyl Esters: Application to the Synthesis of Stegobiol and Serricorole
  作者：Pilar Gil、Jesús Razkin、Alberto González

  DOI：10.1055/s-1998-2052

  日期：1998.4

  β-Hydroxy-α-methyl esters have been obtained in a stereocontrolled manner and high enantiomeric and diastereomeric purity from commercially available methyl 3-oxopentanoate and methyl 3-oxobutanoate. The key step is the catalytic hydrogenation of the carbonyl group using (R)- or (S)-BINAP-Ru as chiral catalyst followed by asymmetric alkylation. Stegobiol and serricorole, components of the sex pheromone of the drugstore beetle, Stegobium paniceum (L.) and cigarette beetle, Lasioderma serricorne (F.), have been prepared from these chiral building blocks without the need for stoichiometric amounts of chiral auxiliaries.

  利用市售的甲基3-氧代戊酸酯和甲基3-氧代丁酸酯，可以通过立体控制的方式合成具有高对映异构体纯度和非对映异构体纯度的β-羟基-α-甲酯。关键步骤是使用手性催化剂(R)-或(S)-BINAP-Ru对羰基进行催化氢化，随后进行不对称烷基化。药物甲虫（Stegobium paniceum L.）和烟甲虫（Lasioderma serricorne F.）的性信息素成分Stegobiol和Serricorole就是从这些手性构建模块中合成的，无需使用等量的手性辅助剂。
• Regio- and Stereochemical Study of Sex Pheromone of Pine Sawfly;<i>Diprion</i><i>nipponica</i>
  作者：Akira Tai、Emi Syouno、Kazuki Tanaka、Morifumi Fujita、Takashi Sugimura、Yasutomo Higashiura、Masashi Kakizaki、Hideho Hara、Tikahiko Naito

  DOI：10.1246/bcsj.75.111

  日期：2002.1

  Regio- and stereoisomers of 1,2,ω-trimethyldecyl propionate (ω = 5–9) were prepared from stereochemically pure chiral building blocks as sex pheromone candidates of a pine sawfly; Diprion nipponica. Among the synthesized candidates, (1S,2R,8S)-1,2,8-trimethyldecyl propionate was found to be the sex pheromone of D. nipponica, based on compatibility of its GC-MS data with that of the extract of females

  1,2,ω-丙酸三甲基癸酯 (ω = 5–9) 的区域异构体和立体异构体是从立体化学纯手性构件中制备的，作为松叶蜂的性信息素候选物；Diprion nipponica。在合成的候选物中，根据其 GC-MS 数据与雌性提取物的 GC-MS 数据的兼容性，发现 (1S,2R,8S)-1,2,8-trimethyldecyl propionate 是 D. nipponica 的性信息素，及其在野外生物测定中显着的高信息素活性。合成化合物的现场生物测定还表明，(1S,2R,8R)-1,2,8-丙酸三甲基癸酯、(1S,2R,7S)-1,2,7-丙酸三甲酯和 (1S,2R, 6S)-1,2,6-trimethyldecyl propionate 可以作为信息素模拟物在一定程度上吸引雄性锯蝇。
• Field and Electroantennogram Responses of the Pine Sawfly, Diprion nipponica, to Chiral Synthetic Pheromone Candidates.
  作者：Akira TAI、Yasutomo HIGASHIURA、Masashi KAKIZAKI、Tikahiko NAITO、Kazuki TANAKA、Morifumi FUJITA、Takashi SUGIMURA、Hideho HARA、Naotaka HAYASHI

  DOI：10.1271/bbb.62.607

  日期：——

  (1S, 2R, 6RS)-1,2,6-Trimethyldecyl propionate, a lower homolog of the sex pheromone of known sawflies, strongly attracted Diprion nipponica, a popular species in Japan.

  (1S, 2R, 6RS)-1,2,6-三甲基癸基丙酸酯，作为一种已知松锯角叶蜂性信息素的低级同系物，对日本常见种日本松锯蜂表现出强烈的吸引作用。
• Tai, Akira; Morimoto, Naotake; Yoshikawa, Masato, Agricultural and Biological Chemistry, 1990, vol. 54, # 7, p. 1753 - 1762
  作者：Tai, Akira、Morimoto, Naotake、Yoshikawa, Masato、Uehara, Kazuya、Sugimura, Takashi、Kikukawa, Tadashi

  DOI：——

  日期：——