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8-tert-Butylspiro<4.5>decane-1,4-dione | 154029-97-7

中文名称
——
中文别名
——
英文名称
8-tert-Butylspiro<4.5>decane-1,4-dione
英文别名
Spiro[4.5]decane-1,4-dione, 8-(1,1-dimethylethyl)-;8-tert-butylspiro[4.5]decane-1,4-dione
8-tert-Butylspiro<4.5>decane-1,4-dione化学式
CAS
154029-97-7
化学式
C14H22O2
mdl
——
分子量
222.327
InChiKey
SGDUBGMJRIJPDQ-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    3
  • 重原子数:
    16
  • 可旋转键数:
    1
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.86
  • 拓扑面积:
    34.1
  • 氢给体数:
    0
  • 氢受体数:
    2

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
    4-叔丁基环己酮 4-tercbutyl-cyclohexanone 98-53-3 C10H18O 154.252

反应信息

  • 作为反应物:
    描述:
    8-tert-Butylspiro<4.5>decane-1,4-dione 在 baker' syeast 、 Triton X-100 、 蔗糖 作用下, 以 乙醇 为溶剂, 反应 48.0h, 以50%的产率得到(S)-8-tert-Butyl-4-hydroxy-spiro[4.5]decan-1-one
    参考文献:
    名称:
    面包酵母还原螺[4.5]癸烷-1,4-二酮衍生物的对映体和非对映体选择性
    摘要:
    通过面包酵母介导的减少是在五个螺[4.5]癸烷-1,4-二酮衍生物进行4,9,12,15,和18。对映选择性一直很高,但这与面部非对映选择性无关,其范围从非常高到零。在某些情况下,酵母介导的还原反应的面部选择性低于NaBH 4。4的还原产物在几个步骤中转化为对映体富集的双环中间体5形式,用于合成角三喹烷戊烯1。酵母介导的螺酮21还原 证明了赤道羰基的还原是非常优选的反应方式。
    DOI:
    10.1016/0957-4166(96)00430-2
  • 作为产物:
    描述:
    (1'α,4'α)-2-(4-tert-Butyl-1-hydroxycyclohexyl)-2-hydroxycyclobutanone 在 三氟化硼乙醚 作用下, 以 二氯甲烷 为溶剂, 反应 17.5h, 以100%的产率得到8-tert-Butylspiro<4.5>decane-1,4-dione
    参考文献:
    名称:
    Lewis Acid Catalyzed Geminal Acylation Reaction of Ketones with 1,2-Bis[(trimethylsilyl)oxy]cyclobutene: Direct Formation of 2,2-Disubstituted 1,3-Cyclopentanediones
    摘要:
    Ketones reacted with 1,2-bis((trimethylsilyl)oxy)cyclobutene (1) under catalysis by boron trifluoride etherate to yield 2,2-disubstituted 1,3-cyclopentanedione products via silylated cyclobutanone intermediates in a two-step, one-pot process. In many instances addition of a small amount of water to the reaction medium after completion of the first step assisted the subsequent rearrangement to the product, such that reversion of the intermediate to the starting ketone became an insignificant process. Yields were best with cyclohexanones (>90%), but steric hindrance and conjugated double bonds reduced yields considerably.
    DOI:
    10.1021/jo00085a041
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文献信息

  • Facial selectivity in nucleophilic reactions of spirocyclic ketones can be controlled by a distant, orthogonal double bond
    作者:Pei-Ying Liu、D. Jean Burnell
    DOI:10.1039/c39940001183
    日期:——
    Spiro[4.5]dec-7-ene-1,4-dione and derivatives substituted at C-7, C-8, and/or C-9 gave products of reaction with methyllithium and with sodium borohydride that in every instance favoured nucleophilic carbonyl attack on the face syn to the double bond; the results are consistent with stereoelectronic control, and the selectivity correlates with a difference in the abilities of the orthogonal C–C bond to donate electron density.
    在C-7、C-8和/或C-9上被取代的螺[4.5]癸-7-烯-1,4-二酮及其衍生物与甲基锂和硼氢化钠反应,在每种情况下都倾向于对双键的同侧进行亲核羰基攻击;结果与立体电子控制一致,选择性与正交C-C键的供电子密度能力差异相关。
  • Elliott, Christine E.; Miller, David O.; Burnell, D. Jean, Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, vol. 2, # 2, p. 217 - 226
    作者:Elliott, Christine E.、Miller, David O.、Burnell, D. Jean
    DOI:——
    日期:——
  • Lewis Acid Catalyzed Geminal Acylation Reaction of Ketones with 1,2-Bis[(trimethylsilyl)oxy]cyclobutene: Direct Formation of 2,2-Disubstituted 1,3-Cyclopentanediones
    作者:Tracy J. Jenkins、D. Jean Burnell
    DOI:10.1021/jo00085a041
    日期:1994.3
    Ketones reacted with 1,2-bis((trimethylsilyl)oxy)cyclobutene (1) under catalysis by boron trifluoride etherate to yield 2,2-disubstituted 1,3-cyclopentanedione products via silylated cyclobutanone intermediates in a two-step, one-pot process. In many instances addition of a small amount of water to the reaction medium after completion of the first step assisted the subsequent rearrangement to the product, such that reversion of the intermediate to the starting ketone became an insignificant process. Yields were best with cyclohexanones (>90%), but steric hindrance and conjugated double bonds reduced yields considerably.
  • Enantio- and diastereoselectivity in the reduction of spiro[4.5]decane-1,4-dione derivatives with baker's yeast
    作者:Yan-Yi Zhu、D. Jean Burnell
    DOI:10.1016/0957-4166(96)00430-2
    日期:1996.11
    Reductions mediated by baker's yeast were carried out on five spiro[4.5]decane-1,4-dione derivatives 4, 9, 12, 15, and 18. Enantioselectivity was always very high, but this did not correlate with the facial diastereoselectivity, which ranged from very high to zero. In some instances, the facial selectivity of the yeast-mediated reduction was lower than that of NaBH4. The reduction product of 4 was
    通过面包酵母介导的减少是在五个螺[4.5]癸烷-1,4-二酮衍生物进行4,9,12,15,和18。对映选择性一直很高,但这与面部非对映选择性无关,其范围从非常高到零。在某些情况下,酵母介导的还原反应的面部选择性低于NaBH 4。4的还原产物在几个步骤中转化为对映体富集的双环中间体5形式,用于合成角三喹烷戊烯1。酵母介导的螺酮21还原 证明了赤道羰基的还原是非常优选的反应方式。
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