1-iodo<3-tetrahydro-2H-pyran-2-yl>oxybutane | 77610-97-0

• 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-iodo<3-tetrahydro-2H-pyran-2-yl>oxybutane
• 英文别名: (R)-3-(tetrahydropyran-2'-yloxy)-1-iodobutane；(R)-1-iodo-3-(tetrahydropyran-2-yloxy)butane；(R)-3-tetrahydropyran-2'-yloxy-1-iodobutane；(R)-1-iodo-3-(tetrahydropyranyloxy)butane；(R)-3-(Tetrahydropyran-2'-yl)butyl iodide；(R)-3-(tetrahydropyranyloxy)butyl iodide；2-[(2R)-4-iodobutan-2-yl]oxyoxane
• CAS: 77610-97-0
• 化学式: C₉H₁₇IO₂
• 分子量: 284.137
• InChiKey: VPLTVSSMWHTNGF-VEDVMXKPSA-N

物化性质

• 沸点：
  288.6±35.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-iodo<3-tetrahydro-2H-pyran-2-yl>oxybutane 在 sodium hydroxide 、 18-冠醚-6 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 105.0h， 生成 (7R)-1-(3-methyloxiran-2-yl)-7-(oxan-2-yloxy)octan-3-one
  参考文献：
  名称：

  Diastereo- and enantioselective routes to some 2,8-dimethyl-1,7-dioxaspiro[5.5]undecanols. Absolute stereochemistry of (E,E,E)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-3-ol and of (E,E)-8-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)methanol present in Bactrocera cucumis

  摘要：

  Routes to the four regioisomeric 2,8-dimethyl-1,7-dioxaspiro[5.5]undecanols have been developed, and in the racemic series, mercury(II)-mediated reactions of appropriate dienone, hydroxy enone, dienedione, and hydroxy dienone systems have been exploited. Most of the epimeric pairs of alcohols (i.e. axial or equatorial) in the E,E, E,Z, or Z,E spiroacetal ring systems have been characterized by detailed H-1, C-13, and correlated NMR spectroscopy and mass spectrometry. Key enantiomers of these alcohols have been obtained by elaborating chiral starting materials such as D-mannitol, L-arabinose, poly(hydroxybutyrate), and in the case of the 5-hydroxy derivative, mandelonitrile lyase mediated formation of a key chiral cyanohydrin was employed. Most of the alcohols, as their trifluoroacetates, are resolved (into enantiomers) on a Lipodex A GC column, thus facilitating their identification from natural sources. In this way, the absolute configurations of a number of 2,8-dimethyl-1,7-dioxaspiro[5.5]undecanols present in the rectal gland secretion of Bactrocera cucumis (cucumber fly) have been determined.

  DOI：

  10.1021/jo00038a027
• 作为产物：
  描述：

  (R)-3-tetrahydropyranyloxy-1-butanol 在 碳酸氢钠 、 sodium iodide 作用下， 以 吡啶 、 丙酮 为溶剂， 反应 31.5h， 生成 1-iodo<3-tetrahydro-2H-pyran-2-yl>oxybutane
  参考文献：
  名称：

  以微生物来源的手性化合物为原料合成西部玉米根虫的（2r，8r）-和（2s，8r）-8-甲基-2-癸醇的丙酸酯

  摘要：

  由（R）-（+）-香茅醇合成西部玉米根虫（Diabrotica virgifera Le Counte）的引诱剂，（2R，8R）-和（2S，8R）-8-甲基-2-癸醇的丙酸酯。和微生物来源的β-羟基丁酸乙酯的对映体。

  DOI：

  10.1016/s0040-4020(01)91175-5

文献信息

• Alkylation reactions of anions derived from 2-benzenesulphonyl tetrahydropyran and their application to spiroketal syntiesis
  作者：Steven V. Ley、Barry Lygo、Francine Sternfeld、Anne Wonnacott

  DOI：10.1016/s0040-4020(01)87660-2

  日期：1986.1

  Deprotonation of (1) follwed by alkylation with carbonyl compounds or halides gave cyclic enol ether addition products by spontaneous elimination of benzenesulphinic acid. Interception of the initial addition products with aldehydes by reductive desulphonylation to give alkylated tetrahydropyran derivatives proeeeded in moderate yield using sodium naphthalenide. Several of the cystic enol ether addition products

  3,4-二氢-2H-吡喃或2-甲氧基四氢吡喃与苯磺酸反应生成2-苯磺酰基四氢吡喃（1）。（1）通过与羰基化合物或卤化物进行烷基化反应进行脱质子化，通过自发消除生成环状烯醇醚加成产物苯磺酸。通过萘二甲磺酸钠的还原性去磺酰化作用，将起始的加成产物与醛类截获，以得到中等收率的烷基化四氢吡喃衍生物。几个囊性烯醇醚加成产物进一步转化成spiroketals包括来自天然产物的信息素的合成和。
• Synthesis and Stereochemistry of Insect Derived Spiroacetals with Branched Carbon Skeletons
  作者：Yong Q. Tu、Achim Hübener、Hesheng Zhang、Christopher J. Moore、Mary T. Fletcher、Patricia Hayes、Konrad Dettner、Wittko Francke、Christopher S. P. McErlean、William Kitching

  DOI：10.1055/s-2000-8232

  日期：——

  7-dioxoaspiro[5.5]undecane system and are certain stereoisomers of the 2,4,8-trimethyl derivative, from the aposematic shield bug, Cantao parentum (White), and a 2,2,8-trimethyl derivative from the rove beetle, Ontholestes murinus (L.). The 1,6-dioxaspiro[4.5]decane system is represented by a stereoisomer of the 2,3,7-trimethyl derivative in the Cantao species. The elucidation of their structures and stereochemistry

  大约三十种结构不同的螺缩醛已从昆虫中表征，但只有三种具有分支的碳骨架。两种基于 1,7-二氧杂螺[5.5]十一烷系统，是 2,4,8-三甲基衍生物的某些立体异构体，来自 aposematic shield bug, Cantao parentum (White)，以及 2,2,8-来自流浪甲虫 Ontholestes murinus (L.) 的三甲基衍生物。1,6-二氧杂螺[4.5]癸烷系统由Cantao物种中的2,3,7-三甲基衍生物的立体异构体表示。描述了通过光谱、合成和对映选择性气相色谱对它们的结构和立体化学的阐明。
• Monooxygenase Stereoselectivity in the Biosynthesis of Stereoisomeric Spiroacetals in the Cucumber Fly, <i>Bactrocera </i><i>c</i><i>ucumis</i>
  作者：Christopher S. P. McErlean、Mary T. Fletcher、Barry J. Wood、James J. De Voss、William Kitching

  DOI：10.1021/ol0263090

  日期：2002.8.1

  [reaction: see text] The stereoselectivity of hydroxylation of alkyltetrahydropyran-2-ols (or their biological equivalents) in the formation of stereoisomers of 2,8-dimethyl-1,7-dioxaspiro[5.5]undecanes in male Bactrocera cucumis has been investigated. Racemic, (6R)-, and (6S)-6-methyl-2-[5-(2)H(1)]-n-pentyltetrahydropyran-2-ol was administered under an [(18)O(2)]-enriched atmosphere. The stereochemistry

  [反应：参见文本]研究了在黄瓜雄性小球藻中形成2,8-二甲基-1,7-二氧杂螺[5.5]十一烷的立体异构体时烷基四氢吡喃-2-醇（或其生物等效物）羟基化的立体选择性。 。在[（18）O（2）]下施用外消旋，（6R）-和（6S）-6-甲基-2- [5-（2）H（1）]-正戊基四氢吡喃-2-醇气氛浓郁。通过组合的对映选择性GC-MS监测生成的螺缩醛的立体化学和同位素组成。单加氧酶强烈偏爱（6S）-底物，并主要提供（S）-醇，然后提供（2S，6R，8S）-2,8-二甲基-1,7-二氧杂螺[5.5]十一烷。（2S，6S，8R）和（2R，6S，8S）（E，Z）异构体似乎主要来自（6S）-四氢吡喃酚的（R）-羟基化反应。
• Synthesis of three stereoisomeric forms of 2,8-dimethyl-1,7-dioxaspiro[5.5]undecane, the main component of the cephalic secretion of andrena wilkella
  作者：Kenji Mori、Kaichi Tanida

  DOI：10.1016/s0040-4020(01)98857-x

  日期：1981.1

  Three stereoisomers of 2,8-dimethyl-1,7-dioxaspiro[5,5]undecane were synthesized from acetoacetic ester by utilizing its yeast reduction and dianion alkylation.

  利用乙酰乙酸酯的酵母还原和二价阴离子烷基化反应，从乙酰乙酸酯合成了2,8-二甲基-1,7-二氧杂螺[5,5]十一烷的三种立体异构体。
• Synthesis of the enantiomers of cis-2-methyl-5-hexanolide, the major component of the sex pheromone of the carpenter bee
  作者：Kenji Mori、Shuji Senda

  DOI：10.1016/s0040-4020(01)96497-x

  日期：1985.1

  and the enantiomers of methyl β-hydroxyisobutyrate. The specific rotations of our samples were [α]D±91.0-93.5° (CHCl3), while the reported values of the samples prepared by resolution or asymmetric synthesis were ±64.5–65.6°.

  （2R，5S）-2-甲基-5-己内酯及其对映体以（S）-乳酸乙酯和β-羟基异丁酸甲酯的对映体为原料，以高光学纯度（⩾98-99％ee）合成。我们样品的比旋光度为[α] D ±91.0-93.5°（CHCl 3），而通过拆分或不对称合成制备的样品的报告值为±64.5–65.6°。